Herbicidal sulfonamides

ABSTRACT

N-(heterocyclicaminocarbonyl)aryl and pyridylsulfonamides, useful for the regulation of plant growth and as pre-emergence and post-emergence herbicides.

RELATED APPLICATIONS

This application is a continuation-in-part of my copending applicationU.S. Ser. No. 109,262, filed Jan. 18, 1980, now abandoned, which is acontinuation-in-part of U.S. Ser. No. 068,658, filed Aug. 28, 1979, nowabandoned, which is a continuation-in-part of U.S. Ser. No. 014,201,filed Feb. 22, 1979, now abandoned.

BACKGROUND OF THE INVENTION

This invention relates to N-(heterocyclicaminocarbonyl)aryl andpyridylsulfonamide agricultural chemicals.

French Pat. No. 1,468,747 discloses the following para-substitutedphenylsulfonamides, useful as antidiabetic agents: ##STR1## wherein R═H,halogen, CF₃ or alkyl.

Logemann et al. Chem. Ab., 53, 18052 g (1959), disclose a number ofsulfonamides, including uracil derivatives and those having the formula:##STR2##

wherein R is butyl, phenyl or ##STR3## and R₁ is hydrogen or methyl.When tested for hypoglycemic effect in rats (oral doses of 25 mg/100 g),the compounds in which R is butyl or phenyl were most potent. The otherswere of low potency or inactive.

Wojciechowski, J. Acta. Polon. Pharm. 19, p. 121-5 (1962) [Chem. Ab., 591633 e] describes the synthesis ofN-[(2,6-dimethoxypyrimidin-4-yl)aminocarbonyl]-4-methylbenzenesulfonamide:##STR4## Based upon similarity to a known compound, the author predictedhypoglycemic activity for the foregoing compound.

Netherlands Pat. No. 121,788, published Sept. 15, 1966, teaches thepreparation of compounds of Formula (i), and their use as general orselective herbicides, ##STR5## wherein

R₁ and R₂ may independently be alkyl of 1-4 carbon atoms; and

R₃ and R₄ may independently be hydrogen, chlorine or alkyl of 1-4 carbonatoms.

U.S. Pat. No. 3,637,366 discloses compounds having the formula: ##STR6##wherein R₁ is hydrogen or lower saturated acyl, and R₂ is hydrogen,2-pyrimidinyl, pyridyl, amidino, acetyl or carbamoyl. The disclosedcompounds are said to provide control of crabgrass, cress, endive,clover and Poa annua.

Substituted pyrimidinyl sulfonyureas of the following formula, which arealso para-substituted on the phenyl ring, are disclosed in Farmco Ed.Sci., 12, 586 (1957) [Chem. Ab., 53, 18052 g (1959)]: ##STR7## where R═Hor CH₃.

The presence of undesired vegetation causes substantial damage to usefulcrops, especially agricultural products that satisfy man's basic foodand fiber needs, such as cotton, rice, corn, wheat, and the like. Thecurrent population explosion and concomitant world food and fibershortage demand improvements in the efficiency of producing these crops.Preventing or minimizing the loss of a portion of such valuable crops bykilling, or inhibiting the growth of undesired vegetation is one way ofimproving this efficiency.

A wide variety of materials useful for killing or inhibiting(controlling) the growth of undesired vegetation is available; suchmaterials are commonly referred to as herbicides. Some weeds, (such asnutsedge) are very difficult to control; many of the herbicides that areused to control nutsedge are so nonselective that they cause damage tothe crops themselves. Thus, a need exists for active herbicides whichcause minimal damage to the crops.

SUMMARY OF THE INVENTION

This invention relates to novel compounds of Formulas I and II and theiragriculturally suitable salts, to agricultural compositions containingthem and to their method of use as herbicides. Some of the compounds ofFormulas I and II have utility for selective weed control in crops suchas soybeans. In addition, compounds of Formula II and those compounds ofFormula I in which W is sulfur are useful as intermediates to compoundsof Formula I in which W is oxygen. ##STR8## wherein ##STR9##

R₂ is H, CH₃, OCH₃, F, Cl, Br, NO₂, CF₃, COR₅, S(O)_(m) R₁₀, SO₂ NR₁₀R₁₁, SO₂ OCH₂ CF₃, SO₂ OCH₂ CCl₃ or SO₂ N(OCH₃)CH₃ ;

R₃ is H, F, Cl, Br, alkyl C₁ -C₄ or CH₃ O;

R₄ is H, Cl, Br, F, alkyl C₁ -C₄, alkoxy C₁ -C₄, NO₂, CO₂ R₆ or R₁₃--S--;

R₅ is alkoxy C₁ -C₆ ; alkenyloxy C₃ -C₆ ; haloalkoxy C₂ -C₆ substitutedwith 1 to 3 halogens selected from Cl, F and Br; cycloalkoxy C₅ -C₆ ;O--CH₂ CH₂ O)_(n) R₇ ; OCH₂ CH₂ CH₂ OR₇ ; NR₈ R₉ ; N(OCH₃)CH₃ or C₁ -C₄alkylthio;

R₆ is alkyl C₁ -C₆ ;

R₇ is alkyl C₁ -C₂ ;

R₈ and R₉ are independently H or alkyl C₁ -C₄ or R₈ and R₉ may be takentogether to be (CH₂)₄, (CH₂)₅ or O(CH₂ CH₂ --)₂ ; and

R₈ can also be ##STR10##

R₁₀ and R₁₁ are independently C₁ -C₆ alkyl or C₃ -C₄ alkenyl or R₁₀ andR₁₁ can be taken together to be (CH₂)₄, (CH₂)₅ or O(CH₂ CH₂)₂ ;

R₁₂ is C₁ -C₁₂ alkyl; CH₂ CH₂ OCH₃ ; CH₂ CH₂ OCH₂ CH₃ ; CH₂ CH₂ CH₂ OCH₃; ##STR11##

R₁₃ is C₁ -C₃ alkyl;

R₁₄ is H, F, Cl, Br, NO₂, CN, CF₃, C₁ -C₃ alkyl, OCH₃ or CH₃ S;

R₁₅ is H, F, Cl, Br, CH₃ or OCH₃ ;

X is H, CH₃, CH₃ O, Cl or OCH₂ CH₃ ;

Y is CH₂ or O;

A is CO₂ H, CO₂ B, CONH₂, phenyl, CN, C₂ -C₄ alkenyl, C₂ -C₄ alkynyl,phenyl substituted with one or two methyl groups or with one or twochlorines;

B is C₁ -C₄ alkyl;

m is 0, 1 or 2;

n is 1 or 2;

Z is 0 or 1;

W is oxygen or sulfur; provided that

(i) when R₁ is ##STR12## then

R₂ is NO₂, COR₅, SO₂ NR₁₀ R₁₁, SO₂ N(CH₃)(OCH₃) or SO₂ R₁₀ ;

R₄ is other than H; and

X is CH₃ or OCH₃ ;

(ii) when W is sulfur; then Y is oxygen and their agricuturally suitablesalts.

Compounds of Formula Ia and IIa are also novel and are useful asintermediates to herbicidal compounds of Formula I in which W is oxygen.##STR13##

R, R₂, R₃, R₄, R₅, R₆, R₇, R₈, R₉, R₁₀, R₁₁, R₁₂, R₁₃, R₁₄, R₁₅, X, A,B, m, n and Z are as previously defined; provided that

when R₁ " is ##STR14## then

R₂ is NO₂, COR₅, SO₂ NR₁₀ R₁₁, SO₂ N(CH)₃ (OCH₃) or SO₂ R₁₀ ;

R₄ is other than H; and

X is CH₃ or OCH₃.

Preferred in order of increasing preference for reasons of biologicalactivity or ease of synthesis or both are the following groups ofcompounds:

(1) Compounds of Formula I wherein W is oxygen;

(2) Compounds of Preferred (1) wherein ##STR15##

(3) Compounds of Preferred (2) wherein ##STR16##

(4) Compounds of Preferred (3) where X is H, CH₃ or OCH₃ ;

(5) Compounds of Preferred (4) wherein R₂ is NO₂, COR₅, SO₂ NR₁₀ R₁₁,SO₂ R₁₀, SO₂ N(OCH₃)(CH₃) and R₁₀ and R₁₁ are CH₃ or CH₃ CH₂ ;

(6) Compounds of Preferred (5) wherein R₃ is H; and

(7) Compounds of Preferred (6) wherein R₅ is C₁ -C₃ alkoxy or allyloxy.

Specifically preferred for their outstanding herbicidal activity orhighly favorable cost or both are:

N-[(6,7-Dihydro-4-methyl-5H-cyclopentapyrimidin-2-yl)-aminocarbonyl]-2-nitrobenzenesulfonamide;

2-{[(6,7-Dihydro-4-methyl-5H-cyclopentapyrimidin-2-yl)-aminocarbonyl]aminosulfonyl}benzoicacid, methyl ester;

N-[(6,7-Dihydro-4-methoxy-5H-cyclopentapyrimidin-2-yl)-aminocarbonyl]-2-nitrobenzenesulfonamide;

2-Chloro-N-[(5,6-dihydro-4-methylfuro[2,3-d]pyrimidin-2-yl)aminocarbonyl]benzenesulfonamide;

2-{[(6,7-Dihydro-4-methyl-5H-cyclopentapyrimidin-2-yl)aminocarbonyl]aminosulfonyl}benzoicacid, ethyl ester;

2-{[(5,6-Dihydro-4-methylfuro[2,3-d]pyrimidin-2-yl)-aminocarbonyl]aminosulfonyl}benzoicacid, ethyl ester;

N-[(5,6-Dihydro-4-methylfuro[2,3-d]pyrimidin-2-yl)-aminocarbonyl]-2-nitrobenzenesulfonamide;

2-{[(5,6-Dihydro-4-methylfuro[2,3-d]pyrimidin-2-yl)-aminocarbonyl]aminosulfonyl}benzoicacid, methyl ester;

N'-[(5,6-Dihydro-4-methylfuro[2,3-d]pyrimidin-2-yl)-aminocarbonyl]-N,N-dimethyl-1,2-benzenedisulfonamide;

2-{[(5,6-Dihydro-4-methoxyfuro[2,3-d]pyrimidin-2-yl)aminocarbonyl]aminosulfonyl}benzoicacid, methyl ester;

2-[[(5,6-Dihydro-4-methoxyfuro[2,3-d]pyrimidin-2-yl)-aminocarbonyl]aminosulfonyl]benzenecarbothioicacid, methyl ester;

1-[2-[[(5,6-Dihydro-4-methoxyfuro[2,3-d]pyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzoyl]pyrrolidine;

2-[[(5,6-Dihydro-4-methylfuro[2,3-d]pyrimidin-2-yl)-aminocarbonyl]aminosulfonyl]-N,N-dimethylbenzamide;

2-{[(4-Chloro-5,6-dihydrofuro[2,3-d]pyrimidin-2-yl)-aminocarbonyl]aminosulfonyl}benzoicacid, methyl ester;

2-{[(6,7-Dihydro-4-methyl-5H-pyrano[2,3-d]pyrimidin-2-yl)aminocarbonyl]aminosulfonyl}benzoicacid, methyl ester; and

2-{[(6,7-Dihydro-4-methoxy-5H-pyrano[2,3-d]pyrimidin-2-yl)aminocarbonyl]aminosulfonyl}benzoicacid, methyl ester.

Synthesis

As shown in Equation 1, the compounds of Formulas I and Ia can beprepared by combining an appropriate 2-aminopyrimidine of Formula IIwith an appropriately substituted sulfonyl isocyanate or isothiocyanateof Formula IV; R, X, Y and W being as previously defined and q being 1or 2. ##STR17##

The reaction is best carried out in inert aprotic organic solvents suchas methylene chloride, tetrahydrofuran or acetonitrile, at ambientpressure and temperature. The mode of addition is not critical; however,it is often convenient to add the sulfonyl isocyanate to a stirredsuspension of the aminopyrimidine. Since such isocyanates usually areliquids, their addition can be easily controlled.

The reaction is generally exothermic. In some cases, the desired productis insoluble in the warm reaction medium and crystallizes from it inpure form. Products soluble in the reaction medium are isolated byevaporation of the solvent, trituration of the solid residue withsolvents such as 1-chlorobutane or ethyl ether, and filtration.

As shown in Equation 2, the compounds of Formulas II and IIa can beprepared by reacting an appropriately substituted carbamimidothioic acidsalt of Formula V with an alkylating agent of Formula VI: ##STR18##wherein R, R₁₂, X and Y are as previously defined; D is a sulfate orhalogen, such as Cl, Br or I; M is an alkali or alkaline earth metal, qis 1 or 2, and s is an integer corresponding to the valence of D.

The reaction is best carried out in inert aprotic organic solvents suchas tetrahydrofuran or diethyl ether at temperatures between about 25°and 100° C. and at ambient pressure. The mode of addition is notcritical; however, it is often convenient to add the alkylating agent insolution to a stirred suspension of said salt. The end product isisolated by evaporation of the solvent and recrystallization of theresidue from a solvent such as acetonitrile or ethanol.

The metal salts of Formula V can be prepared by treating thecorresponding sulfonylthiourea (Formula VII, Equation 3) with a solutionof an alkali metal or alkaline earth metal salt having an anionsufficiently basic to abstract the proton (e.g. hydroxide, alkoxide,carbonate, or hydride). As shown in Equation 3, the sulfonylthiourea VIIcan be prepared by combining an appropriately substituted sulfonylisothiocyanate of Formula VIII with an appropriate 2-aminoheterocycle ofFormula III; R, X, Y and q being as previously defined: ##STR19##

The reaction is best carried out in inert aprotic organic solvents suchas methylene chloride, tetrahydrofuran or acetonitrile, at ambientpressure and temperature. The mode of addition is not critical; however,it is often convenient to add the isothiocyanate to a stirred suspensionof the aminoheterocycle. Since such isothiocyanates usually are liquids,their addition is more easily controlled. Catalysts, such as1,4-diazabicyclo[2.2.2]octane or dibutyltindilaurate, may be used.

In some cases, sulfonylthioureas of Formula VII are more convenientlyprepared, as shown in Equation 4, by reacting an appropriatelysubstituted sulfonamide of Formula IX with the appropriate2-isothiocyanatoheterocycle of Formula X; R, X, Y and q being aspreviously defined; ##STR20##

The preparation of 2-isothiocyanatoheterocycles of Formula X is taughtin Japanese patent Kokai 51-143686.

The preparation of the sulfonyl thioureas of Formula VII and reactantstherefor is described in said U.S. Applications Ser. Nos. 824,805 and840,389, the contents of which in that connection are incorporatedherein by reference.

The compounds of Formulas II and IIa may also be prepared as shown inEquation 5. ##STR21##

A compound of Formula XI is reacted with the salt of the heterocyclicamine at temperatures of 0° to 100° in a suitable solvent e.g.,dimethylformamide, dimethylsulfoxide or an ethereal solvent e.g.,tetrahydrofuran; R, R₁₂, X, Y and q are as previously defined. M' is analkali metal cation, e.g., sodium or potassium.

Compounds of Formula XI may be prepared as described in Chem. Ber. 99,2885 (1966).

a. Sulfonyl isocyanate or Isothiocyanate Intermediates

The intermediate aryl sulfonyl isocyanate of Formula IV (W═O) can beprepared by reacting corresponding aryl sulfonamides with phosgene inthe presence of n-butyl isocyanate at reflux in a solvent such aschlorobenzene, according to the procedure of H. Ulrich and A. A. Y.Sayigh, Newer Methods of Preparative Organic Chemistry, Vol. VI, p.223-241, Academic Press, New York and London, W. Foerst Ed. Theintermediate pyridyl sulfonyl isocyanates of Formula IV (W═O) can beprepared by reacting an N-(alkylaminocarbonyl)pyridinesulfonamide withphosgene as described in U.S. patent application No. 966,258, thedisclosure of which is hereby incorporated by reference. TheN-(alkylaminocarbonyl)pyridinesulfonamide can be prepared, as describedin U.S. Ser. No. 966,258, by the reaction of a pyridinesulfonamide, analkyl isocyanate and an anhydrous base in an anhydrous solvent.

The preparation of sulfonamides from ammonium hydroxide and sulfonylchloride is widely reported in the literature, e.g., Crossley et al., J.Am. Chem. Soc. 60, 2223 (1938). The preparation of pyridylsulfonamide isdescribed in G. Machek, Monatsch 2, 84 (1939) and L. Thunus and C. L.Lapiere, Ann. Farn 33, 663 (1975).

Certain sulfonyl chlorides are best prepared by chlorosulfonation of asubstituted benzene in carbon tetrachloride according to the teaching ofH. T. Clarke et al., Org. Synth. Coll. Vol. 1, 2nd Ed., 1941, p. 85.Other benzenesulfonyl chlorides are best made by diazotization of theappropriate aniline with sodium nitrite in HCl, followed by reaction ofthe diazonium salt with sulfur dioxide and cuprous chloride in aceticacid according to the teaching of H. L. Yale and F. Sowinski, J. Org.Chem. 25, 1824 (1960). The preparation of pyridyl sulfonyl chlorides isdescribed in Chem. Abs. 88, 190603 m (1978).

Sulfonylisothiocyanates of Formula IV (W═S) can be prepared by treatmentof sulfonamides with carbon disulfide and potassium hydroxide followedby reaction of the dipotassium salt with phosgene according to theteaching of K. Hartke, Arch. Pharm., 229, 174 (1966).

Pyridine sulfonylisothiocyanates can be prepared according to theprocedure taught by K. Dickere and E. Kuhle in U.S. Patent 3,346,590. Asuitable pyridinesulfonyliminodithiocarbonate is reacted with phosgenein the presence of a solvent such as toluene or xylene.

A different method is used for preparing the intermediate sulfonylisocyanate of Formula IV (W═O) when the intermediate is ano-sulfamoylbenzenesulfonyl isocyanate. This method is illustrated byEquations 2a-e.

    ______________________________________                                        Equation 2a-d                                                                 ______________________________________                                        (2a)                                                                                 ##STR22##                                                                                           ##STR23##                                        (2b)                                                                                 ##STR24##                                                                                           ##STR25##                                        (2c)                                                                                 ##STR26##                                                                                           ##STR27##                                        (2d)                                                                                 ##STR28##                                                                                           ##STR29##                                        (2e)                                                                                 ##STR30##                                                                                           ##STR31##                                        ______________________________________                                    

wherein

R₃, R₁₀ and R₁₁ are as defined previously.

In step (2a), the o-nitrobenzenesulfonyl chlorides in Formula a, whichare well-known in the art, are treated with an amine, R₁₀ R₁₁ NH, in aninert organic solvent such as methylene chloride, ethyl ether, ortetrahydrofuran at 0°-50°. The amine may be taken in excess to act as anacid acceptor; alternatively, a tertiary amine such as triethylamine orpyridine may be used as an acid acceptor. The by-product aminehydrochloride is filtered off or washed out of the solvent with waterand the product isolated by evaporation of the solvent.

The reduction described in step (2b) is accomplished by treating asolution of the compounds of Formula b in a solvent such as ethanol,ethyl acetate, or DMF, in a pressure vessel with 100-1000 pounds persquare inch of hydrogen at 80°-150° in the presence of a hydrogenationcatalyst such as 5-10% palladium absorbed on carbon. When thetheoretical amount of hydrogen has been absorbed, the solution is cooledand the catalyst is removed by filtration. The product is then isolatedby evaporation of the solvent.

The diazotization and coupling with sulfur dioxide, described in step(2c), is accomplished in the following manner. A solution of theo-sulfamoyl aniline of Formula c in a mixture of concentratedhydrochloric acid and glacial acetic acid is treated with a solution ofsodium nitrite in water at -5° to 0°. After stirring for 10-15 minutesat 0° to insure complete diazotization, this solution is added to amixture of an excess of sulfur dioxide and a catalytic amount of cuprouschloride in glacial acetic acid at 0°-5°. The temperature is kept at0°-5° for 1/4 to 1 hour and is then raised to 20°-25° and held at thattemperature for 2-4 hours. This solution is then poured into a largeexcess of ice water. The sulfonyl chloride products, d, can be isolatedby filtration or by extraction into solvent such as ethyl ether ormethylene chloride followed by evaporation of the solvent.

The amination described in step (2d) is conveniently carried out bytreating a solution of the sulfonyl chloride of Formula d with an excessof anhydrous ammonia in a solvent such as ethyl ether or methylenechloride at 0°-25°. If the product sulfonamide is insoluble it may beisolated by filtration followed by washing out the salts with water. Ifthe product sulfonamide is soluble in the reaction solution, it may beisolated by filtering off the precipitated ammonium chloride andevaporating the solvent.

Sulfonylisocyanates of Formula IV in which R₂ is SO₂ OCH₂ CCl₃, SO₂ OCH₂CF₃ or SO₂ N(CH₃)OCH₃ can be prepared by a sequence analogous to thatshown in Equations 2a-e.

b. Aminopyrimidine Intermediates

The synthesis of heterocyclic amine derivatives such as those depictedby Formula III has been reviewed in "The Chemistry of HeterocyclicCompounds", a series published by Interscience Publ., New York andLondon. Aminopyrimidines are described by D. J. Brown in "ThePyrimidines", Vol. XVI of the above series.

Preparation of compounds of Formula III varies according to thedefinition of X, Y and q.

Braker, Sheehan, Spitzmiller and Lott, J. Am. Chem. Soc. 69, 3072 (1947)describe the preparation of6,7-dihydro-4-methoxy-5H-cyclopentapyrimidin-2-amine by the followingsequence of reactions. ##STR32##

An analogous sequence of reactions can be used to prepare5,6,7,8-tetrahydro-4-methoxy-2-quinazolinamine. ##STR33##

Mitter and Bhattacharya, Quart. J. Indian Chem. Soc. 4, 152 (1927)describe the preparation of5,6,7,8-tetrahydro-4-methyl-2-quinazolinamine as follows: ##STR34##

Similarly, 6,7-dihydro-4-methyl-5H-cyclopentapyrimidin-2-amine can beprepared by the condensation of 2-acetylcyclopentanone with guanidinecarbonate, but preferably by heating in dimethylsulfoxide at 135° forseveral hours. ##STR35##

Shrage and Hitchings, J. Org. Chem. 16, 1153 (1951) describe thepreparation of 5,6-dihydro-4-methylfuro [2,3-d]pyrimidin-2-amine by thefollowing sequence of reactions ##STR36##

An analogous sequence of reactions can be used to prepare6,7-dihydro-4-methyl-5H-pyrano[2,3-d]pyrimidin-2-amine starting with2-acetyl-8 valerolactone [Korte and Wusten, Tetrahedron 19, 1423(1963)]. ##STR37##

5,6-Dihydro-4-hydroxyfuro[2,3-d]pyrimidine-2-amine [Svab, Budesinski andVavrina, Collection Czech. Chem. Commun. 32, 1582 (1967)] can beconverted to 2-amino-5-(2-chloroethyl)-4,6-dichloropyrimidine by heatingwith phosphorus oxychloride. The product can be subsequently cyclized bytreatment with two equivalents of aqueous sodium hydroxide to afford4-chloro-5,6-dihydrofuro[2,3-d]pyrimidin-2-amine, which is thenconverted to 5,6-dihydro-4-methoxyfuro[2,3-d]pyrimidin-2-amine byheating with excess sodium methoxide in methanol. ##STR38##

6,7-Dihydro-4-hydroxy-5H-pyrano[2,3-d]pyrimidin-2-amine can be preparedfrom diethyl 3-chloropropylmalonate, guanidine carbonate and sodiumethoxide in ethanol. Treatment of the product ##STR39## with phosphorusoxychloride gives 4-chloro-6,7-dihydro-5H-pyrano[2,3-d]pyrimidin-2-amineand subsequent reaction with sodium methoxide in refluxing methanolaffords 6,7-dihydro-4-methoxy-5H-pyrano[2,3-d]pyrimidin-2-amine.

Compounds of Formulas I, Ia, II and IIa where X is ethoxy can beprepared by a procedure analogous to the methoxy derivatives.

Caldwell, Kornfeld and Donnell, J. Am. Chem. Soc. 63, 2188 (1941),describe the preparation of 6,7-dihydro-5H-cyclopentapyrimidin-2-amineby the following sequence of reactions. ##STR40##

Fissekis, Myles and Brown, J. Org. Chem. 29, 2670 (1964), describe thepreparation of 2-amino-4-hydroxy-5-(2-hydroxyethyl)pyrimidine which canbe converted to 5,6-dihydrofuro[2,3-d]pyrimidin-2-amine by dehydration.##STR41##

c. Special Situations

When R₅ is NR₈ R₉ in Formula I or Ia, the compounds of this inventioncan be prepared by reacting the appropriate compound of Formula XIIIwith the appropriate alkylaminodialkylaluminum derivative of FormulaXIV. This is illustrated in Equation 6, wherein y'1 to 6. ##STR42##

The compounds of Formula XIII are prepared in the manner describedabove. The intermediate alkylaminodialkylaluminum derivatives of FormulaXIV, which are prepared according to A. Basha, M. Lipton and S. Weinreb,Tetrahedron Letters, 4171 (1977), are treated with suspensions of theappropriate esters in toluene or a similar inert solvent, and themixture is refluxed for one to six hours. The product can be isolated byevaporation of the toluene, adding methylene chloride, water andhydrochloric acid to decompose the residual reaction mass and extractingthe product into methylene chloride. Evaporation of the methylenechloride yields the desired product, sufficiently pure for the purposesof this invention.

When R₅ is C₁ -C₄ alkylthio, these compounds can be prepared from theesters of this invention wherein R₅ is C₁ -C₄ alkoxy by the reaction ofthe esters with the appropriate dialkylaluminum alkylthiolate accordingto Equation 7. ##STR43##

The intermediate aluminum thiolates can be prepared according to R. P.Hatch and S. W. Weinreb, Journal of Organic Chemistry, Vol. 42, 3960(1977). The reaction of the thiolate with the ester of this invention isbest carried out in a neutral solvent such as toluene or xylene atreflux for one to three hours. Best results are obtained when thealuminum thiolate compound is present in excess of the stoichiometricamount required.

An alternate route to prepare compounds where R₅ is a secondary alcoholresidue involves the reaction of the appropriate dialkylaluminumalcoholate and an ester of this invention wherein R' is a lower primaryalkyl group, preferably methyl, according to Equation 8. ##STR44##

The reaction is carried out in a neutral solvent such as toluene with aboiling point sufficiently high to bring about the desired reactionduring reflux. The dialkylaluminum alcoholate being present in greaterthan an equivalent amount to the ester for best yields. After refluxingfor 1-15 hours, the reaction mixture is decomposed with dilutehydrochloric acid and the product extracted into methylene chloride.Evaporation of the methylene chloride yields the desired compoundsufficiently pure for the purposes of this invention. The product can betriturated with a solvent, e.g. 1-chlorobutane to remove impurities.

Thioureas and isothioureas may be readily converted to theircorresponding ureas, as depicted in Equation 9, with oxidizing agentssuch as hydrogen peroxide or mercuric oxide. This method of preparingureas is known in the literature and is described in "Open-ChainNitrogen Compounds" by P. A. S. Smith (W. A. Benjamin, New York, 1965)p. 274. ##STR45##

The disclosures of all references cited above are herein incorporated byreference.

Agriculturally suitable salts of compounds of Formula I or II are alsouseful herbicides and can be prepared by a number of ways known to theart. For example, metal salts can be made by treating compounds ofFormula I or II with a solution of alkali or alkaline earth metal salthaving a sufficiently basic anion (e.g., hydroxide, alkoxide, carbonateor hydride). Quaternary amine salts can be made by similar techniques.

Salts of compounds of Formula I or II can also be prepared by exchangeof one cation for another Cationic exchange can be effected by directtreatment of an aqueous solution of a salt of a compound of Formula I orII (e.g., alkali metal of quaternary amine salt) with a solutioncontaining the cation to be exchanged. This method is most effectivewhen the desired salt containing the exchanged cation is insoluble inwater, e.g., a copper salt, and can be separated by filtration.

Exchange may also be effected by passing an aqueous solution of a saltof a compound of Formula I or II (e.g., an alkali metal or quaternaryamine salt) through a column packed with a cation exchange resincontaining the cation to be exchanged. In this method, the cation of theresin is exchanged for that of the original salt and the desired productis eluted from the column. This method is particularly useful when thedesired salt is water soluble, e.g, a potassium, sodium or calcium salt.

Acid addition salts, useful in this invention, can be obtained byreacting a compound of Formula I or II with a suitable acid, e.g.,p-toluenesulfonic acid, trichloroacetic acid or the like.

The compounds of this invention and their preparation are furtherillustrated by the following examples wherein temperatures are given indegrees centigrade.

EXAMPLE 1 2-Amino-5-(2-chloroethyl)-4,6-dichloropyrimidine

A mixture of 10 g of 6,7-dihydro-4-hydroxyfuro-[2,3-d]pyrimidin-2-amine,100 ml of phosphorus oxychloride and 0.5 ml N,N-dimethylaniline wereheated at 100°-110° for 2 hours. Excess phosphorus oxychloride wasremoved under reduced pressure and the residue was mixed with 500 g icethen neutralized to pH 7 with ammonium hydroxide solution. The solidproduct was collected by filtration, rinsed with water and dried toyield 12 g of 2-amino-5-(2-chloroethyl)-4,6-di-chloropyrimidine, m.p.210°-213°. The mass spectrum exhibited a parent ion at m/e 225, 227, 229and showed two triplets at 3.40 and 3.88 ppm by nuclear magneticresonance spectrum (60 MHz), indicating the title compound.

EXAMPLE 2 4-Chloro-5,6-dihydrofuro[2,3-d]pyrimidin-2-amine

A suspension of 6.0 g of2-amino-5-(2-chloroethyl)-4,6-dichloropyrimidine, 29 ml of 2 N aqueoussodium hydroxide solution, 35 ml water and 75 ml of t-butanol was heatedto reflux (60°) for 24 hours then cooled. The solid was collected byfiltration, rinsed with water and dried to yield 2.4 g of4-chloro-5,6-dihydrofuro[2,3-d]pyrimidin-2-amine, m.p. 258°-263°. Theproduct showed characteristic triplet absorption bands at 3.40 and 5.10ppm in the nuclear magnetic resonance spectrum (60 MHz), indicating thetitle compound.

EXAMPLE 3 5,6-Dihydro-4-methoxyfuro[2,3-d]pyrimidin-2-amine

To a suspension of 27 g of4-chloro-5,6-dihydrofuro[2,3-d]pyrimidin-2-amine in 500 ml of anhydrousmethanol was added 22 g of sodium methoxide and the mixture was heatedto reflux (66°) for 5.5 hours. The solvent was then removed underreduced pressure and the residue triturated with water (500 ml) thenfiltered and rinsed well with water. The solid was air dried to give 20g of 5,6-dihydro-4-methoxyfuro[2,3-d]pyrimidin-2-amine, m.p. 172°-177°.Two triplet absorptions at 3.42 and 5.02 ppm and a singlet absorption at4.21 ppm in the nuclear magnetic resonance spectrum (60 MHz), indicatedthe title compound.

EXAMPLE 42-[[6,7-Dihydro-4-methyl-5H-cyclopentapyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzoicacid, cyclopentyl ester

To 20 ml of dry toluene was added 2.4 ml of 2 M trimethylaluminum intoluene under a nitrogen atmosphere. Subsequently, 0.82 g cyclopentanolin 1 ml toluene was added via syringe and the mixture stirred at ambienttemperature for 15 minutes. After addition of 1.56 g of methyl2-[[(6,7-dihydro-4-methyl-5H-cyclopentapyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzoateto the mixture, the reaction was heated to 80° for 3.5 hours. Themixture was then cooled in ice while B 40 ml of 5% aqueous hydrochloricacid was added. Ethyl acetate was then added and shaking of the twophase mixture resulted in the crystallization of the product which wascollected and dried to yield 1.5 g of2-[[(6,7-dihydro-4-methyl-5H-cyclopentapyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzoicacid, cyclopentyl, ester, m.p. 183°-184°. The product showedcharacteristic absorptions at 3120, 1725, 1720 cm⁻¹ in the infraredspectrum and at 1.7-2.35, 2.50, 2.95, 5.4, 7.6, 8.4, 8.5 and 13.0 ppm inthe nuclear magnetic resonance spectrum (60 MHz), indicating the titlecompound.

EXAMPLE 5N-[(6,7-Dihydro-4-methyl-5H-cyclopentapyrimidin-2-yl)-aminocarbonyl]-2-nitrobenzenesulfonamide

To a dry, stirred solution of 10 g of6,7-dihydro-4-methyl-5H-cyclopentapyrimidin-2-amine in 800 ml ofmethylene chloride at ambient temperature and pressure was added 14.9 gof 2-nitrobenzenesulfonylisocyanate. The resulting mixture was stirredat reflux temperature (42°) for 2 hours after which the methylenechloride was removed under reduced pressure. The resulting solid wastriturated with methanol or 1-chlorobutane and filtered to yield 15 g ofN-[(6,7-dihydro-4-methyl-5H-cyclopentapyrimidin-2-yl)aminocarbonyl]-2-nitrobenzene-sulfonamide,m.p. 202°-205°. The product showed characteristic absorption bands inthe infrared spectrum at 1675 cm⁻¹ and at 1.7, 3.2 and 7.7 to 8.5 ppmsby nuclear magnetic resonance spectrum (60 MHz), indicating the titlecompound.

By application of one or more of the procedures of Examples 1 to 5and/or the methods described above, and using the appropriate reactants,the compounds of Table I can be prepared.

                                      TABLE I-A                                   __________________________________________________________________________     ##STR46##                                                                       R.sub.2      R.sub.3   W  Y   m.p.                                         __________________________________________________________________________    H               H         O  CH.sub.2                                         Cl              H         O  CH.sub.2                                                                          190-192°                              F               H         O  CH.sub.2                                         Br              H         O  CH.sub.2                                         SCH.sub.3       H         O  CH.sub.2                                         SO.sub.2 CH.sub.3                                                                             H         O  CH.sub.2                                         CF.sub.3        H         O  CH.sub.2                                         NO.sub.2        H         O  CH.sub.2                                                                          202-205°                              CO.sub.2 CH.sub.3                                                                             H         O  CH.sub.2                                                                          193-194°                              CO.sub.2 CH.sub.2 CH.sub.3                                                                    H         O  CH.sub.2                                                                          153-154°                              CO.sub.2 CH.sub.2 CH.sub.2 Cl                                                                 H         O  CH.sub.2                                         CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                           H         O  CH.sub.2                                         CO.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                          H         O  CH.sub.2                                         CO.sub.2 CH.sub.2 CH.sub.2 Br                                                                 H         O  CH.sub.2                                         CO.sub.2 CH(CH.sub.3).sub.2                                                                   H         O  CH.sub.2                                                                          207-210°                              CO.sub.2 CH.sub.2 CHCH.sub.2                                                                  H         O  CH.sub.2                                                                          167-172°                              CO.sub.2 CH.sub.2 CF.sub.3                                                                    H         O  CH.sub.2                                         CO.sub.2 (CH.sub.2).sub.3 CH.sub.3                                                            H         O  CH.sub.2                                                                          160-161°                              CO.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3                                                        H         O  CH.sub.2                                         CO.sub.2 CH(CH.sub.2 CH.sub.3).sub.2                                                          H         O  CH.sub.2                                         CO.sub.2 CH.sub.2 C(CH.sub.3).sub.3                                                           H         O  CH.sub.2                                         CO.sub.2 CH.sub.2 CHCHCH.sub.3                                                                H         O  CH.sub.2                                         CO.sub.2 CH(CH.sub.3)CHCH.sub.2                                                               H         O  CH.sub.2                                                                          190-191°                              CO.sub.2 CH.sub.2 CHCH(CH.sub.2).sub.2 CH.sub.3                                               H         O  CH.sub.2                                         CO.sub.2 (CH.sub.2).sub.4 Cl                                                                  H         O  CH.sub.2                                         CO.sub.2 (CH.sub.2).sub.6 Cl                                                                  H         O  CH.sub.2                                          ##STR47##      H         O  CH.sub.2                                                                          183-184°                               ##STR48##      H         O  CH.sub.2                                                                          193-195°                              CO.sub.2 (CH.sub.2 CH.sub.2 O).sub.2 CH.sub. 3                                                H         O  O   CH.sub.2                                     CO.sub.2 (CH.sub.2 CH.sub.2 O).sub.2 C.sub.2 H.sub.5                                          H         O  CH.sub.2                                         CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                 H         O  CH.sub.2                                         CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 OC.sub.2 H.sub.5                                          H         O  CH.sub.2                                         CON(CH.sub.3).sub.2                                                                           H         O  CH.sub.2                                                                          170-172°                              CON(C.sub.2 H.sub.5).sub.2                                                                    H         O  CH.sub.2                                                                          166-169°                               ##STR49##      H         O  CH.sub.2                                         CONH.sub.2      H         O  CH.sub.2                                         CONHCH.sub.3    H         O  CH.sub.2                                         CO.sub.2 CH.sub.2 CH.sub.2 OC.sub.2 H.sub.5                                                   H         O  CH.sub.2                                         CON(CH(CH.sub.3).sub.2).sub.2                                                                 H         O  CH.sub.2                                          ##STR50##      H         O  CH.sub.2                                         CON(CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3).sub.2                                                H         O  CH.sub.2                                          ##STR51##      H         O  CH.sub.2                                          ##STR52##      H         O  CH.sub.2                                                                          189-190°                              Cl              5-Cl      O  CH.sub.2                                                                          201-203°                              Cl              6-Cl      O  CH.sub.2                                         Cl              4-Cl      O  CH.sub.2                                         Cl              3-Cl      O  CH.sub.2                                         F               5-Cl      O  CH.sub.2                                         F               3-Cl      O  CH.sub.2                                         F               4-Cl      O  CH.sub.2                                         F               5-F       O  CH.sub.2                                         Cl              5-OCH.sub.3                                                                             O  CH.sub.2                                         Cl              5-CH(CH.sub.3).sub.2                                                                    O  CH.sub.2                                         Cl              4-CH.sub.3                                                                              O  CH.sub.2                                         Cl              4-F       O  CH.sub.2                                         Cl              5-Br      O  CH.sub.2                                         Cl              6-CH.sub.3                                                                              O  CH.sub.2                                         NO.sub.2        5-Cl      O  CH.sub.2                                         NO.sub.2        6-Cl      O  CH.sub.2                                                                          200-202°                              NO.sub.2        5-F       O  CH.sub.2                                         Cl              5-CH(CH.sub.3)C.sub.2 H.sub.5                                                           O  CH.sub.2                                         Br              5-F       O  CH.sub.2                                         SCH.sub.3       5-Cl      O  CH.sub.2                                         Cl              5-C.sub.2 H.sub.5                                                                       O  CH.sub.2                                          ##STR53##      H         O  CH.sub.2                                                                          122-123°                              SCH.sub.3       4-Cl      O  CH.sub.2                                         SO.sub.2 CH.sub.3                                                                             H         O  CH.sub.2                                                                          183-187°                              SO.sub.2 CH.sub.3                                                                             6-Cl      O  CH.sub.2                                         SCH.sub.3       6-Cl      O  CH.sub.2                                         SCH.sub.3       4-OCH.sub.3                                                                             O  CH.sub.2                                         CF.sub.3        5-Cl      O  CH.sub.2                                         CF.sub.3        5-CH.sub.3                                                                              O  CH.sub.2                                         CF.sub.3        5-F       O  CH.sub.2                                         CF.sub.3        4-Cl      O  CH.sub.2                                         CF.sub.3        4-CH.sub.3                                                                              O  CH.sub.2                                         CO.sub.2 CH.sub.3                                                                             5-CH.sub.3                                                                              O  CH.sub.2                                         CO.sub.2 CH.sub.3                                                                             6-CH.sub.3                                                                              O  CH.sub.2                                         CO.sub.2 CH.sub.3                                                                             5-Cl      O  CH.sub.2                                         CO.sub.2 CH.sub.3                                                                             3-Cl      O  CH.sub.2                                         CO.sub.2 CH.sub.3                                                                             6-Cl      O  CH.sub.2                                         CO.sub.2 CH.sub.3                                                                             4-CH.sub.3                                                                              O  CH.sub.2                                         SO.sub.2 CH.sub.2 CH.sub.3                                                                    H         O  CH.sub.2                                         SO.sub.2 CH.sub.2 CHCH.sub.2                                                                  H         O  CH.sub.2                                         SOCH.sub.3      H         O  CH.sub.2                                         SOCH.sub.2 CH.sub.3                                                                           5-Cl      O  CH.sub.2                                          ##STR54##      H         O  CH.sub.2                                                                          207-208° (d)                           ##STR55##      H         O  CH.sub.2                                          ##STR56##      6-Cl      O  CH.sub.2                                          ##STR57##      5-F       O  CH.sub.2                                         SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                           H         O  CH.sub.2                                                                          189-190°                               ##STR58##      H         O  CH.sub.2                                                                          179-180°                               ##STR59##      5-OCH.sub.3                                                                             O  CH.sub.2                                          ##STR60##      H         O  CH.sub.2                                         SO.sub.2 OCH.sub.2 CF.sub.3      175-177°                                              H         O  CH.sub.2                                         SO.sub.2 OCH.sub.2 CCl.sub.3                                                                  H         O  CH.sub.2                                          ##STR61##      H         O  CH.sub.2                                         H               H         O  O   193-194° (d)                          Cl              H         O  O   202-205°                              F               H         O  O                                                Br              H         O  O                                                SCH.sub.3       H         O  O                                                SO.sub.2 CH.sub.3                                                                             H         O  O                                                CF.sub.3        H         O  O                                                NO.sub.2        H         O  O   180-187°                              CO.sub.2 CH.sub.3                                                                             H         O  O   194.5-197°                            CO.sub.2 CH.sub.2 CH.sub.3                                                                    H         O  O   187-188°                              CO.sub.2 CH.sub.2 CH.sub.2 Cl                                                                 H         O  O                                                CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                           H         O  O                                                CO.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                          H         O  O                                                CO.sub.2 CH.sub.2 CH.sub.2 Br                                                                 H         O  O                                                SO.sub.2 OCH.sub.2 CF.sub.3                                                                   H         O  O                                                SO.sub.2 OCH.sub.2 CCl.sub.3                                                                  H         O  O                                                 ##STR62##      H         O  O                                                CH.sub.3        H         O  O   170-173° (d)                          CO.sub.2 CH(CH.sub.3).sub.2                                                                   H         O  O   196-199°                              CO.sub.2 CH.sub.2 CHCH.sub.2                                                                  H         O  O   205-206°                              CO.sub.2 CH.sub.2 CF.sub.3                                                                    H         O  O                                                CO.sub.2 (CH.sub.2).sub.3 CH.sub.3                                                            H         O  O   163-165°                              CO.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3                                                        H         O  O                                                CO.sub.2 CH(CH.sub.2 CH.sub.3).sub.2                                                          H         O  O                                                CO.sub.2 CH.sub.2 C(CH.sub.3).sub.3                                                           H         O  O                                                CO.sub.2 CH.sub.2 CHCHCH.sub.3                                                                H         O  O                                                CO.sub.2 CH(CH.sub.3)CHCH.sub.2                                                               H         O  O   192-194°                              CO.sub.2 CH.sub.2 CHCH(CH.sub.2).sub.2 CH.sub.3                                               H         O  O                                                CO.sub.2 (CH.sub.2).sub.4 Cl                                                                  H         O  O                                                CO.sub.2 (CH.sub.2).sub.6 Cl                                                                  H         O  O                                                 ##STR63##      H         O  O   169-171°                               ##STR64##      H         O  O   178-179°                              CO.sub.2 (CH.sub.2 CH.sub.2 O).sub.2 CH.sub.3                                                 H         O  O                                                CO.sub.2 (CH.sub.2 CH.sub.2 O).sub.2 C.sub.2 H.sub.5                                          H         O  O                                                CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                 H         O  O                                                CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 OC.sub.2 H.sub.5                                          H         O  O                                                CON(CH.sub.3).sub.2                                                                           H         O  O   189-191°                              CON(C.sub.2 H.sub.5).sub.2                                                                    H         O  O                                                 ##STR65##      H         O  O                                                CONH.sub.2      H         O  O                                                CONHCH.sub.3    H         O  O                                                 ##STR66##      H         O  O   192-193°                              CO.sub.2 CH.sub.2 CH.sub.2 OC.sub.2 H.sub.5                                                   H         O  O                                                CON(CH(CH.sub.3).sub.2).sub.2                                                                 H         O  O                                                 ##STR67##      H         O  O                                                CON(CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3).sub.2                                                H         O  O                                                 ##STR68##      H         O  O                                                Cl              5-Cl      O  O                                                Cl              6-Cl      O  O                                                Cl              4-Cl      O  O                                                Cl              3-Cl      O  O                                                F               5-Cl      O  O                                                F               3-Cl      O  O                                                F               4-Cl      O  O                                                F               5-F       O  O                                                Cl              5-OCH.sub.3                                                                             O  O                                                Cl              5-CH(CH.sub.3).sub.2                                                                    O  O                                                Cl              4-CH.sub.3                                                                              O  O                                                Cl              4-F       O  O                                                Cl              5-Br      O  O                                                Cl              6-CH.sub.3                                                                              O  O                                                NO.sub.2        5-Cl      O  O                                                NO.sub.2        6-Cl      O  O                                                NO.sub.2        5-F       O  O                                                Cl              5-CH(CH.sub.3)C.sub.2 H.sub.5                                                           O  O                                                Br              5-F       O  O                                                SCH.sub.3       5-Cl      O  O                                                Cl              5-C.sub.2 H.sub.5                                                                       O  O                                                SCH.sub.3       4-Cl      O  O                                                SO.sub.2 CH.sub.3                                                                             5-Cl      O  O                                                SO.sub.2 CH.sub.3                                                                             6-Cl      O  O                                                SCH.sub.3       6-Cl      O  O                                                SCH.sub.3       4-OCH.sub.3                                                                             O  O                                                CF.sub.3        5-Cl      O  O                                                CF.sub.3        5-CH.sub.3                                                                              O  O                                                CF.sub.3        5-F       O  O                                                CF.sub.3        4-Cl      O  O                                                CF.sub.3        4-CH.sub.3                                                                              O  O                                                CO.sub.2 CH.sub.3                                                                             5-CH.sub.3                                                                              O  O                                                CO.sub.2 CH.sub.3                                                                             6-CH.sub.3                                                                              O  O                                                CO.sub.2 CH.sub.3                                                                             5-Cl      O  O                                                CO.sub.2 CH.sub.3                                                                             3-Cl      O  O                                                CO.sub.2 CH.sub.3                                                                             6-Cl      O  O                                                CO.sub.2 CH.sub.3                                                                             4-CH.sub.3                                                                              O  O                                                SOCH.sub.3      H         O  O                                                SOCH.sub.2 CHCH.sub.2                                                                         5-Cl      O  O                                                 ##STR69##      H         O  O   188-193°                               ##STR70##      5-F       O  O                                                 ##STR71##      6-CH.sub.3                                                                              O  O                                                 ##STR72##      4-OCH.sub.3                                                                             O  O                                                 ##STR73##      H         O  O                                                 ##STR74##      5-Cl      O  O                                                SO.sub.2 N(C.sub.2 H.sub.5).sub.2                                                             H         O  O                                                 ##STR75##      H         O  O                                                H               H         S  O                                                CH.sub.3        H         S  O                                                OCH.sub.3       H         S  O                                                Cl              H         S  O   190-191° (d)                          F               H         S  O                                                CF.sub.3        H         S  O                                                NO.sub.2        H         S  O                                                CO.sub.2 CH.sub.3                                                                             H         S  O                                                CO.sub.2 (CH.sub.2).sub.3 CH.sub.3                                                            H         S  O                                                CO.sub.2 (CH.sub.2).sub.3 Cl                                                                  H         S  O                                                CO.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                          H         S  O                                                 ##STR76##      H         S  O                                                CON(C.sub.2 H.sub.5).sub.2                                                                    H         S  O                                                CONHCH.sub.3    H         S  O                                                CON(OCH.sub.3)CH.sub.3                                                                        H         S  O                                                SO.sub.2 N(C.sub.2 H.sub.5).sub.2                                                             H         S  O                                                SO.sub.2 OCH.sub.2 Cl.sub.3                                                                   H         S  O                                                Cl              5-Cl      S  O                                                OCH.sub.3       5-OCH.sub.3                                                                             S  O                                                CO.sub.2 CH.sub.3                                                                             4-CH.sub.3                                                                              S  O                                                F               5-F       S  O                                                Cl              6-CH.sub.3                                                                              S  O                                                __________________________________________________________________________

                                      TABLE I-B                                   __________________________________________________________________________     ##STR77##                                                                       R.sub.2      R.sub.3   W  Y   m.p.                                         __________________________________________________________________________    Cl              H         O  CH.sub.2                                                                          224°                                  Cl              5-Cl      O  CH.sub.2                                                                          231.5-232°                            NO.sub.2        H         O  CH.sub.2                                                                          211-212°                              CO.sub.2 CH.sub.3                                                                             H         O  CH.sub.2                                                                          169-184°                              CO.sub.2 CH(CH.sub.3).sub.2                                                                   H         O  CH.sub.2                                                                          207-209°                              F               H         O  CH.sub.2                                         Br              H         O  CH.sub.2                                         SCH.sub.3       H         O  CH.sub.2                                         SO.sub.2 CH.sub.3                                                                             H         O  CH.sub.2                                                                          225-230°                              CF.sub.3        H         O  CH.sub.2                                         CO.sub.2 CH.sub.2 CH.sub.3                                                                    H         O  CH.sub.2                                                                          178-179°                              CO.sub.2 CH.sub.2 CH.sub.2 Cl                                                                 H         O  CH.sub.2                                         CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                           H         O  CH.sub.2                                         CO.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                          H         O  CH.sub.2                                         CO.sub.2 CH.sub.2 CHCH.sub.2                                                                  H         O  CH.sub.2                                                                          137-140°                              CO.sub.2 CH.sub.2 CF.sub.3                                                                    H         O  CH.sub.2                                         CO.sub.2 (CH.sub.2).sub.3 CH.sub.3                                                            H         O  CH.sub.2                                                                          149-151°                              CO.sub.2 (CH.sub.2).sub.5 CH.sub.3                                                            H         O  CH.sub.2                                         CO.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3                                                        H         O  CH.sub.2                                         CO.sub.2 CH(CH.sub.2 CH.sub.3).sub.2                                                          H         O  CH.sub.2                                         CO.sub.2 CH.sub.2 C(CH.sub.3).sub.3                                                           H         O  CH.sub.2                                         CO.sub.2 CH.sub.2 CHCHCH.sub.3                                                                H         O  CH.sub.2                                         H               H         O  CH.sub.2                                         CO.sub.2 CH(CH.sub.3)CHCH.sub.2                                                               H         O  CH.sub.2                                                                          176-177°                              CO.sub.2 CH.sub.2 CHCH(CH.sub.2).sub.2 CH.sub.3                                               H         O  CH.sub.2                                         CO.sub.2 (CH.sub.2).sub.4 Cl                                                                  H         O  CH.sub.2                                         CO.sub.2 (CH.sub.2).sub.6 Cl                                                                  H         O  CH.sub.2                                          ##STR78##      H         O  CH.sub.2                                                                          174-175°                               ##STR79##      H         O  CH.sub.2                                                                          171-172°                              CO.sub.2 (CH.sub.2 CH.sub.2 O).sub.2 CH.sub.3                                                 H         O  CH.sub.2                                         CO.sub.2 (CH.sub.2 CH.sub.2 O).sub.2 C.sub.2 H.sub.5                                          H         O  CH.sub.2                                         CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                 H         O  CH.sub.2                                         CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 OC.sub.2 H.sub.5                                          H         O  CH.sub.2                                         CON(CH.sub.3).sub.2                                                                           H         O  CH.sub.2                                                                          177-178°                              CON(C.sub.2 H.sub.5).sub.2                                                                    H         O  CH.sub.2                                                                          207-208°                               ##STR80##      H         O  CH.sub.2                                         CON(CH(CH.sub.3).sub.2).sub.2                                                                 H         O  CH.sub.2                                          ##STR81##      H         O  CH.sub.2                                         CON(CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3).sub.2                                                H         O  CH.sub.2                                          ##STR82##      H         O  CH.sub.2                                          ##STR83##      H         O  CH.sub.2                                                                          194-195°                               ##STR84##      H         O  CH.sub.2                                                                          193-194°                              Cl              6-Cl      O  CH.sub.2                                         Cl              4-Cl      O  CH.sub.2                                         Cl              3-Cl      O  CH.sub.2                                         F               5-Cl      O  CH.sub.2                                         F               3-Cl      O  CH.sub.2                                         F               4-Cl      O  CH.sub.2                                         F               5-F       O  CH.sub.2                                         Cl              5-OCH.sub.3                                                                             O  CH.sub.2                                         Cl              5-CH(CH.sub.3).sub.2                                                                    O  CH.sub.2                                         Cl              4-CH.sub.3                                                                              O  CH.sub.2                                         Cl              4-F       O  CH.sub.2                                         Cl              5-Br      O  CH.sub.2                                         Cl              6-CH.sub.3                                                                              O  CH.sub.2                                         NO.sub.2        5-Cl      O  CH.sub.2                                         NO.sub.2        6-Cl      O  CH.sub.2                                                                          197-198°                              NO.sub.2        5-F       O  CH.sub.2                                         Cl              5-CH(CH.sub.3)C.sub.2 H.sub.5                                                           O  CH.sub.2                                         Br              5-F       O  CH.sub.2                                         SCH.sub.3       5-Cl      O  CH.sub.2                                         SCH.sub.3       4-Cl      O  CH.sub.2                                         SO.sub.2 CH.sub.3                                                                             5-Cl      O  CH.sub.2                                         SO.sub.2 CH.sub.3                                                                             6-Cl      O  CH.sub.2                                         SCH.sub.3       6-Cl      O  CH.sub.2                                         SCH.sub.3       4-OCH.sub.3                                                                             O  CH.sub.2                                         CF.sub.3        5-Cl      O  CH.sub.2                                         CF.sub.3        5-CH.sub.3                                                                              O  CH.sub.2                                         CF.sub.3        5-F       O  CH.sub.2                                         CF.sub.3        4-Cl      O  CH.sub.2                                         CF.sub.3        4-CH.sub.3                                                                              O  CH.sub.2                                         CO.sub.2 CH.sub.3                                                                             5-CH.sub.3                                                                              O  CH.sub.2                                         CO.sub.2 CH.sub.3                                                                             6-CH.sub.3                                                                              O  CH.sub.2                                         CO.sub.2 CH.sub.3                                                                             5-Cl      O  CH.sub.2                                         CO.sub. 2 CH.sub.3                                                                            3-Cl      O  CH.sub.2                                         CO.sub.2 CH.sub.3                                                                             6-Cl      O  CH.sub.2                                         CO.sub.2 CH.sub.3                                                                             4-CH.sub.3                                                                              O  CH.sub.2                                         SOCH.sub.3      H         O  CH.sub.2                                         SOCH.sub.3      5-Br      O  CH.sub.2                                          ##STR85##      6-CH.sub.3                                                                              O  CH.sub.2                                          ##STR86##      H         O  CH.sub.2                                          ##STR87##      H         O  CH.sub.2                                          ##STR88##      5-Cl      O  CH.sub.2                                          ##STR89##      4-OCH.sub.3                                                                             O  CH.sub.2                                          ##STR90##      H         O  CH.sub.2                                                                          170-171°                               ##STR91##      3-F       O  CH.sub.2                                          ##STR92##      5-CH.sub.2 CH.sub.3 O                                                                   CH.sub.2                                             ##STR93##      H         O  CH.sub.2                                         SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                           H         O  CH.sub.2                                                                          207-212°                               ##STR94##      H         O  CH.sub.2                                         SO.sub.2 OCH.sub.2 CF.sub.3                                                                   5-Cl      O  CH.sub.2                                         SO.sub.2 OCH.sub.2 CCl.sub.3                                                                  3-F       O  CH.sub.2                                         Cl              H         O  O   219-223°                              Cl              5-Cl      O  O                                                NO.sub.2        H         O  O                                                CO.sub.2 CH.sub.3                                                                             H         O  O   203-206°                              CO.sub.2 CH(CH.sub.3).sub.2                                                                   H         O  O   222-224°                              F               H         O  O                                                Br              H         O  O                                                SCH.sub.3       H         O  O                                                SO.sub.2 CH.sub.3                                                                             H         O  O                                                CF.sub.3        H         O  O                                                CO.sub.2 CH.sub.2 CH.sub.3                                                                    H         O  O   211-214°                              CO.sub.2 CH.sub.2 CH.sub.2 Cl                                                                 H         O  O                                                CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                           H         O  O                                                CO.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                          H         O  O                                                CO.sub.2 CH.sub.2 CHCH.sub.2                                                                  H         O  O   193-195°                              CO.sub.2 CH.sub.2 CF.sub.3                                                                    H         O  O                                                CO.sub.2 (CH.sub.2).sub. 3 CH.sub.3                                                           H         O  O   168-171°                              CO.sub.2 (CH.sub.2).sub.5 CH.sub.3                                                            H         O  O                                                CO.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3                                                        H         O  O                                                CO.sub.2 CH(CH.sub.2 CH.sub.3).sub.2                                                          H         O  O                                                CO.sub.2 CH.sub.2 C(CH.sub.3).sub.3                                                           H         O  O                                                CO.sub.2 CH.sub.2 CHCHCH.sub.3                                                                H         O  O                                                H               H         O  O                                                SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                           H         O  O                                                CO.sub.2 CH(CH.sub.3)CHCH.sub.2                                                               H         O  O   182-185°                              CO.sub.2 CH.sub.2 CHCH(CH.sub.2).sub.2 CH.sub.3                                               H         O  O                                                CO.sub.2 (CH.sub.2).sub.4 Cl                                                                  H         O  O                                                CO.sub.2 (CH.sub.2).sub.6 Cl                                                                  H         O  O                                                 ##STR95##      H         O  O   195-197°                               ##STR96##      H         O  O   171-173°                              CO.sub.2 (CH.sub.2 CH.sub.2 O).sub.2 CH.sub.3                                                 H         O  O                                                CO.sub.2 (CH.sub.2 CH.sub.2 O).sub.2 C.sub.2 H.sub.5                                          H         O  O                                                CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                 H         O  O                                                CO.sub.2 CH.sub.2 CH.sub.2 CH.sub. 2 OC.sub.2 H.sub.5                                         H         O  O                                                CON(CH.sub.3).sub.2                                                                           H         O  O   184-186°                              CON(C.sub.2 H.sub.5).sub.2                                                                    H         O  O   188-191°                               ##STR97##      H         O  O                                                CON(CH(CH.sub.3).sub.2).sub.2                                                                 H         O  O                                                 ##STR98##      H         O  O                                                CON(CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3).sub.2                                                H         O  O                                                 ##STR99##      H         O  O                                                 ##STR100##     H         O  O   196-197°                               ##STR101##     H         O  O   190-191°                              Cl              6-Cl      O  O                                                Cl              4-Cl      O  O                                                Cl              3-Cl      O  O                                                F               5-Cl      O  O                                                F               3-Cl      O  O                                                F               4-Cl      O  O                                                F               5-F       O  O                                                Cl              5-OCH.sub.3                                                                             O  O                                                Cl              5-CH(CH.sub.3).sub.2                                                                    O  O                                                Cl              4-CH.sub.3                                                                              O  O                                                Cl              4-F       O  O                                                Cl              5-Br      O  O                                                Cl              6-CH.sub.3                                                                              O  O                                                NO.sub.2        5-Cl      O  O                                                NO.sub. 2       6-Cl      O  O                                                NO.sub.2        5-F       O  O                                                Cl              5-CH(CH.sub.3)C.sub.2 H.sub.5                                                           O  O                                                Br              5-F       O  O                                                SCH.sub.3       5-Cl      O  O                                                SCH.sub.3       4-Cl      O  O                                                SO.sub.2 CH.sub.3                                                                             5-Cl      O  O                                                SO.sub.2 CH.sub.3                                                                             6-Cl      O  O                                                SCH.sub.3       6-Cl      O  O                                                SCH.sub.3       4-OCH.sub.3                                                                             O  O                                                CF.sub.3        5-Cl      O  O                                                CF.sub.3        5-CH.sub.3                                                                              O  O                                                CF.sub.3        5-F       O  O                                                CF.sub.3        4-Cl      O  O                                                CF.sub.3        4-CH.sub.3                                                                              O  O                                                CO.sub.2 CH.sub.3                                                                             5-CH.sub.3                                                                              O  O                                                CO.sub.2 CH.sub.3                                                                             6-CH.sub.3                                                                              O  O                                                CO.sub.2 CH.sub.3                                                                             5-Cl      O  O                                                CO.sub.2 CH.sub.3                                                                             3-Cl      O  O                                                CO.sub.2 CH.sub.3                                                                             6-Cl      O  O                                                CO.sub.2 CH.sub.3                                                                             4-CH.sub.3                                                                              O  O                                                SOCH.sub.3      H         O  O                                                SOCH.sub.3      5-Cl      O  O                                                SOCH.sub.2 CHCH.sub.3                                                                         6-F       O  O                                                 ##STR102##     H         O  O                                                 ##STR103##     H         O  O                                                 ##STR104##     5-OCH.sub.3                                                                             O  O                                                 ##STR105##     3-Br      O  O                                                 ##STR106##     H         O  O   181-182°                               ##STR107##     5-F       O  O                                                 ##STR108##     H         O  O                                                 ##STR109##     6-CH.sub.3                                                                              O  O                                                SO.sub.2 OCH.sub.2 CF.sub.3                                                                   H         O  O                                                SO.sub.2 OCH.sub.2 CCl.sub.3                                                                  5-Cl      O  O                                                 ##STR110##     H         O  O                                                CH.sub.3        H         S  O                                                Cl              H         S  O                                                NO.sub.2        H         S  O                                                CO.sub.2 CH.sub.2 CH.sub.3                                                                    H         S  O                                                SO.sub.2 CH.sub.3                                                                             H         S  O                                                CF.sub.3        H         S  O                                                CO.sub.2 (CH.sub.2).sub.3 OCH.sub.3                                                           H         S  O                                                CO.sub.2 CH.sub.2 CH.sub.2 Cl                                                                 H         S  O                                                CO.sub.2 CH.sub.2 CHCHCH.sub.3                                                                H         S  O                                                CON(OCH.sub.3)CH.sub.3                                                                        H         S  O                                                CON(CH.sub. 3)[CH(CH.sub.3).sub.2 ]                                                           H         S  O                                                 ##STR111##     H         S  O                                                 ##STR112##     H         S  O                                                 ##STR113##     H         S  O                                                SO.sub.2 OCH.sub.2 CCl.sub.3                                                                  H         S  O                                                Cl              5-Cl      S  O                                                NO.sub.2        5-Cl      S  O                                                CO.sub.2 CH.sub.3                                                                             4-Br      S  O                                                SOC.sub.2 H.sub.5                                                                             4-F       S  O                                                 ##STR114##     5-Cl      S  O                                                OCH.sub.3       5-OCH.sub.3                                                                             S  O                                                 ##STR115##     4-CH.sub.3                                                                              S  O                                                SO.sub.2 OCH.sub.2 CF.sub.3                                                                   5-Cl      S  O                                                __________________________________________________________________________

                                      TABLE I-C                                   __________________________________________________________________________     ##STR116##                                                                   R.sub.2         R.sub.3   W  Y   m.p.                                         __________________________________________________________________________    Cl              H         O  CH.sub.2                                                                          193-195°                              Cl              5-Cl      O  CH.sub.2                                         NO.sub.2        H         O  CH.sub.2                                                                          179-184° (d)                          CO.sub.2 CH.sub.3                                                                             H         O  CH.sub.2                                                                          208-209°                              CO.sub.2 CH(CH.sub.3).sub.2                                                                   H         O  CH.sub.2                                         F               H         O  CH.sub.2                                         Br              H         O  CH.sub.2                                         SCH.sub.3       H         O  CH.sub.2                                         SO.sub.2 CH.sub.3                                                                             H         O  CH.sub.2                                         CF.sub.3        H         O  CH.sub.2                                         CO.sub.2 CH.sub.2 CH.sub.3                                                                    H         O  CH.sub.2                                         CO.sub.2 CH.sub.2 CH.sub.2 Cl                                                                 H         O  CH.sub.2                                         CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                           H         O  CH.sub.2                                         CO.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                          H         O  CH.sub.2                                         CO.sub.2 CH(CH.sub.3).sub.2                                                                   H         O  CH.sub.2                                         CO.sub.2 CH.sub.2 CHCH.sub.2                                                                  H         O  CH.sub.2                                         CO.sub.2 CH.sub.2 CF.sub.3                                                                    H         O  CH.sub.2                                         CO.sub.2 (CH.sub.2).sub.3 CH.sub.3                                                            H         O  CH.sub.2                                         CO.sub.2 (CH.sub.2).sub.5 CH.sub.3                                                            H         O  CH.sub.2                                         CO.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3                                                        H         O  CH.sub.2                                         CO.sub.2 CH(CH.sub.2 CH.sub.3).sub.2                                                          H         O  CH.sub.2                                         CO.sub.2 CH.sub.2 C(CH.sub.3).sub.3                                                           H         O  CH.sub.2                                         CO.sub.2 CH.sub.2 CHCHCH.sub.3                                                                H         O  CH.sub.2                                         H               H         O  CH.sub.2                                         CO.sub.2 CH(CH.sub.3)CHCH.sub.2                                                               H         O  CH.sub.2                                         CO.sub.2 CH.sub.2 CHCH(CH.sub.2).sub.2 CH.sub.3                                               H         O  CH.sub.2                                         CO.sub.2 (CH.sub.2).sub.4 Cl                                                                  H         O  CH.sub.2                                         CO.sub.2 (CH.sub.2).sub.6 Cl                                                                  H         O  CH.sub.2                                          ##STR117##     H         O  CH.sub.2                                          ##STR118##     H         O  CH.sub.2                                         CO.sub.2 (CH.sub.2 CH.sub.2 O).sub.2 CH.sub.3                                                 H         O  CH.sub.2                                         CO.sub.2 (CH.sub.2 CH.sub.2 O).sub.2 C.sub.2 H.sub.5                                          H         O  CH.sub.2                                         CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                 H         O  CH.sub.2                                         CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 OC.sub.2 H.sub.5                                          H         O  CH.sub.2                                         CON(CH.sub.3).sub.2                                                                           H         O  CH.sub.2                                         CON(C.sub.2 H.sub.5).sub.2                                                                    H         O  CH.sub.2                                          ##STR119##     H         O  CH.sub.2                                         CON(CH(CH.sub.3).sub.2).sub.2                                                                 H         O  CH.sub.2                                          ##STR120##     H         O  CH.sub.2                                         CON(CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3).sub.2                                                H         O  CH.sub.2                                          ##STR121##     H         O  CH.sub.2                                         Cl              6-Cl      O  CH.sub.2                                         Cl              4-Cl      O  CH.sub.2                                         Cl              3-Cl      O  CH.sub.2                                         F               5-Cl      O  CH.sub.2                                         F               3-Cl      O  CH.sub.2                                         F               4-Cl      O  CH.sub.2                                         F               5-F       O  CH.sub.2                                         Cl              5-OCH.sub.3                                                                             O  CH.sub.2                                         Cl              5-CH(CH.sub.3).sub.2                                                                    O  CH.sub.2                                         Cl              4-CH.sub.3                                                                              O  CH.sub.2                                         Cl              4-F       O  CH.sub.2                                         Cl              5-Br      O  CH.sub.2                                         Cl              6-CH.sub.3                                                                              O  CH.sub.2                                         NO.sub.2        5-Cl      O  CH.sub.2                                         NO.sub.2        6-Cl      O  CH.sub.2                                         NO.sub.2        5-F       O  CH.sub.2                                         Cl              5-CH(CH.sub.3)C.sub.2 H.sub.5                                                           O  CH.sub.2                                         Br              5-F       O  CH.sub.2                                         SCH.sub.3       5-Cl      O  CH.sub.2                                         SCH.sub.3       4-Cl      O  CH.sub.2                                         SO.sub.2 CH.sub.3                                                                             5-Cl      O  CH.sub.2                                         SO.sub.2 CH.sub.3                                                                             6-Cl      O  CH.sub.2                                         SCH.sub.3       6-Cl      O  CH.sub.2                                         SCH.sub.3       4-OCH.sub.3                                                                             O  CH.sub.2                                         CF.sub.3        5-Cl      O  CH.sub.2                                         CF.sub.3        5-CH.sub.3                                                                              O  CH.sub.2                                         CF.sub.3        5-F       O  CH.sub.2                                         CF.sub.3        4-Cl      O  CH.sub.2                                         CF.sub.3        4-CH.sub.3                                                                              O  CH.sub.2                                         CO.sub.2 CH.sub.3                                                                             5-CH.sub.3                                                                              O  CH.sub.2                                         CO.sub.2 CH.sub.3                                                                             6-CH.sub.3                                                                              O  CH.sub.2                                         CO.sub.2 CH.sub.3                                                                             5-Cl      O  CH.sub.2                                         CO.sub.2 CH.sub.3                                                                             3-Cl      O  CH.sub.2                                         CO.sub.2 CH.sub.3                                                                             6-Cl      O  CH.sub.2                                         CO.sub.2 CH.sub.3                                                                             4-CH.sub.3                                                                              O  CH.sub.2                                         SOCH.sub.3      H         O  CH.sub.2                                         SOCH.sub.3      5-Br      O  CH.sub.2                                          ##STR122##     6-CH.sub.3                                                                              O  CH.sub.2                                          ##STR123##     H         O  CH.sub.2                                          ##STR124##     H         O  CH.sub.2                                          ##STR125##     5-Cl      O  CH.sub.2                                          ##STR126##     4-OCH.sub.3                                                                             O  CH.sub.2                                          ##STR127##     H         O  CH.sub.2                                          ##STR128##     3-F       O  CH.sub.2                                          ##STR129##     5-CH.sub.2 CH.sub.3                                                                     O  CH.sub.2                                          ##STR130##     5-Cl      O  CH.sub.2                                         Cl              H         O  O   180-183° (d)                          Cl              5-Cl      O  O                                                NO.sub.2        H         O  O                                                CO.sub.2 CH.sub.3                                                                             H         O  O   206-209° (d)                          CO.sub.2 CH(CH.sub.3).sub.2                                                                   H         O  O                                                F               H         O  O                                                Br              H         O  O                                                SCH.sub.3       H         O  O                                                SO.sub.2 CH.sub.3                                                                             H         O  O                                                CF.sub.3        H         O  O                                                CO.sub.2 CH.sub.2 CH.sub.3                                                                    H         O  O                                                CO.sub.2 CH.sub.2 CH.sub.2 Cl                                                                 H         O  O                                                CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                           H         O  O                                                CO.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                          H         O  O                                                SO.sub.2 OCH.sub.2 CF.sub.3                                                                   H         O  CH.sub.2                                         CO.sub.2 CH.sub.2 CHCH.sub.2                                                                  H         O  O                                                CO.sub.2 CH.sub.2 CF.sub.3                                                                    H         O  O                                                CO.sub.2 (CH.sub.2).sub.3 CH.sub.3                                                            H         O  O                                                CO.sub.2 (CH.sub.2).sub.5 CH.sub.3                                                            H         O  O                                                CO.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3                                                        H         O  O                                                CO.sub.2 CH(CH.sub.2 CH.sub.3).sub.2                                                          H         O  O                                                CO.sub.2 CH.sub.2 C(CH.sub.3).sub.3                                                           H         O  O                                                CO.sub.2 CH.sub.2 CHCHCH.sub.3                                                                H         O  O                                                H               H         O  O                                                 ##STR131##     H         O  O                                                CO.sub.2 CH.sub.2 CHCH(CH.sub.2).sub.2 CH.sub.3                                               H         O  O                                                CO.sub.2 (CH.sub.2).sub.4 Cl                                                                  H         O  O                                                CO.sub.2 (CH.sub.2).sub.6 Cl                                                                  H         O  O                                                 ##STR132##     H         O  O                                                 ##STR133##     H         O  O                                                CO.sub.2 (CH.sub.2 CH.sub.2 O).sub.2 CH.sub.3                                                 H         O  O                                                CO.sub.2 (CH.sub.2 CH.sub.2 O).sub.2 C.sub.2 H.sub.5                                          H         O  O                                                CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                 H         O  O                                                CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 OC.sub.2 H.sub.5                                          H         O  O                                                CON(CH.sub.3).sub.2                                                                           H         O  O                                                CON(C.sub.2 H.sub.5).sub.2                                                                    H         O  O                                                 ##STR134##     H         O  O                                                CON(CH(CH.sub.3).sub.2).sub.2                                                                 H         O  O                                                 ##STR135##     H         O  O                                                CON(CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3).sub.2                                                H         O  O                                                 ##STR136##     H         O  O                                                Cl              6-Cl      O  O                                                Cl              4-Cl      O  O                                                Cl              3-Cl      O  O                                                F               5-Cl      O  O                                                F               3-Cl      O  O                                                F               4-Cl      O  O                                                F               5-F       O  O                                                Cl              5-OCH.sub.3                                                                             O  O                                                Cl              5-CH(CH.sub.3).sub.2                                                                    O  O                                                Cl              4-CH.sub.3                                                                              O  O                                                Cl              4-F       O  O                                                Cl              5-Br      O  O                                                Cl              6-CH.sub.3                                                                              O  O                                                NO.sub.2        5-Cl      O  O                                                NO.sub.2        6-Cl      O  O                                                NO.sub.2        5-F       O  O                                                Cl              5-CH(CH.sub.3)C.sub.2 H.sub.5                                                           O  O                                                Br              5-F       O  O                                                SCH.sub.3       5-Cl      O  O                                                SCH.sub.3       4-Cl      O  O                                                SO.sub.2 CH.sub.3                                                                             5-Cl      O  O                                                SO.sub.2 CH.sub.3                                                                             6-Cl      O  O                                                SCH.sub.3       6-Cl      O  O                                                SCH.sub.3       4-OCH.sub.3                                                                             O  O                                                CF.sub.3        5-Cl      O  O                                                CF.sub.3        5-CH.sub.3                                                                              O  O                                                CF.sub.3        5-F       O  O                                                CF.sub.3        4-Cl      O  O                                                CF.sub.3        4-CH.sub.3                                                                              O  O                                                CO.sub.2 CH.sub.3                                                                             5-CH.sub.3                                                                              O  O                                                CO.sub.2 CH.sub.3                                                                             6-CH.sub.3                                                                              O  O                                                CO.sub.2 CH.sub.3                                                                             5-Cl      O  O                                                CO.sub.2 CH.sub.3                                                                             3-Cl      O  O                                                CO.sub.2 CH.sub.3                                                                             6-Cl      O  O                                                CO.sub.2 CH.sub.3                                                                             4-CH.sub.3                                                                              O  O                                                SOCH.sub.3      H         O  O                                                SOCH.sub.3      5-Cl      O  O                                                SOCH.sub.2 CHCH.sub.3                                                                         6-F       O  O                                                 ##STR137##     H         O  O                                                 ##STR138##     H         O  O                                                 ##STR139##     5-OCH.sub.3                                                                             O  O                                                 ##STR140##     3-Br      O  O                                                 ##STR141##     H         O  O                                                 ##STR142##     5-F       O  O                                                 ##STR143##     H         O  O                                                 ##STR144##     6-CH.sub.3                                                                              O  O                                                 ##STR145##     H         O  O                                                SO.sub.2 OCH.sub.2 CCl.sub.3                                                                  3-Cl      O  O                                                H               H         S  O                                                Cl              H         S  O   104-108° (d)                          F               H         S  O                                                NO.sub.2        H         S  O                                                SCH.sub.3       H         S  O                                                OCH.sub.3       H         S  O                                                SOCH(CH.sub.3).sub.2                                                                          H         S  O                                                CF.sub.3        H         S  O                                                CO.sub.2 CH.sub.3                                                                             H         S  O                                                CO.sub.2 CH.sub.2 CH.sub.2 Br                                                                 H         S  O                                                CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                 H         S  O                                                CO.sub.2 CH.sub.2 CCl.sub.3                                                                   H         S  O                                                CO.sub.2 CH.sub. 2 CHCH.sub.2                                                                 H         S  O                                                CO.sub.2 CH(CH.sub.3).sub.2                                                                   H         S  O                                                CON(OCH.sub.3)CH.sub.3                                                                        H         S  O                                                CON[CH(CH.sub.3).sub.2 ].sub.2                                                                H         S  O                                                 ##STR146##     H         S  O                                                 ##STR147##     H         S  O                                                SO.sub.2 OCH.sub.2 CCl.sub.3                                                                  H         S  O                                                H               5-F       S  O                                                Cl              5-Cl      S  O                                                CO.sub.2 CH.sub.3                                                                             5-OCH.sub.3                                                                             S  O                                                NO.sub.2        6-Cl      S  O                                                OCH.sub.3       5-OCH.sub.3                                                                             S  O                                                SO.sub.2 N(CH.sub.3).sub.2                                                                    4-Cl      S  O                                                CON(CH.sub.3).sub.2                                                                           5-Br      S  O                                                SO.sub.2 OCH.sub.2 CF.sub.3                                                                   5-CH.sub.3                                                                              S  O                                                __________________________________________________________________________

                  TABLE I-D                                                       ______________________________________                                         ##STR148##                                                                    R.sub.2      R.sub.3     W     Y    m.p.                                     ______________________________________                                        CO.sub.2 CH.sub.3                                                                           H           O     CH.sub.2                                                                           190.5-192°                        CO.sub.2 CH.sub.3                                                                           3-Cl        O     CH.sub.2                                      CO.sub.2 CH.sub.3                                                                           4-C.sub.2 H.sub.5                                                                         O     CH.sub.2                                      CO.sub.2 C.sub.2 H.sub.5                                                                    H           O     CH.sub.2                                      CO.sub.2 C.sub.2 H.sub.5                                                                    4-CH.sub.2 CH.sub.2 CH.sub.3                                                              O     CH.sub.2                                      CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                         H           O     CH.sub.2                                      CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                         4-F         O     CH.sub.2                                       ##STR149##   H           O     CH.sub.2                                       ##STR150##   3-Cl        O     CH.sub.2                                      CO.sub.2 (CH.sub.2).sub.4 CHCH.sub.2                                                        H           O     CH.sub.2                                       ##STR151##   H           O     CH.sub.2                                      CO.sub.2 CH.sub.2 CH.sub.2 OC.sub.2 H.sub.5                                                 H           O     CH.sub.2                                      CO.sub.2 (CH.sub.2).sub.3 OCH.sub.3                                                         4-CH.sub.3  O     CH.sub.2                                       ##STR152##   Cl          O     CH.sub.2                                       ##STR153##   H           O     CH.sub.2                                      SO.sub.2 N(CH.sub.3).sub.2                                                                  H           O     CH.sub.2                                      SO.sub.2 N(C.sub.2 H.sub.5).sub.2                                                           H           O     CH.sub.2                                       ##STR154##   H           O     CH.sub.2                                      NO.sub.2      H           O     CH.sub.2                                                                           192-196° (d)                      COSCH.sub.3   H           O     CH.sub.2                                       ##STR155##   5-Cl        O     CH.sub.2                                      COSCH.sub.2 CH.sub.3                                                                        6-OCH.sub.3 O     CH.sub.2                                      CO.sub.2 CH.sub.3                                                                           H           O     O    179-183°                          CO.sub.2 CH.sub.3                                                                           3-Cl        O     O                                             CO.sub.2 CH.sub.3                                                                           4-C.sub.2 H.sub.5                                                                         O     O                                             CO.sub.2 C.sub.2 H.sub.5                                                                    H           O     O    178-182°                          CO.sub.2 C.sub.2 H.sub.5                                                                    4-CH.sub.2 CH.sub.2 CH.sub.3                                                              O     O                                             CO.sub.2 CH.sub.2 CH.sub.2 CH.sub. 3                                                        H           O     O                                             CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                         4-F         O     O                                              ##STR156##   H           O     O                                              ##STR157##   3-Cl        O     O                                             CO.sub.2 (CH.sub.2).sub.4 CHCH.sub.2                                                        H           O     O                                              ##STR158##   H           O     O                                             CO.sub.2 CH.sub.2 CH.sub.2 OC.sub.2 H.sub.5                                                 H           O     O                                             CO.sub.2 (CH.sub.2).sub.3 OCH.sub.3                                                         4-CH.sub.3  O     O                                              ##STR159##   Cl          O     O                                              ##STR160##   H           O     O                                             COSCH.sub.3   H           O     O                                              ##STR161##   3-Br        O     O                                             COSCH.sub.2 CH.sub.2 CH.sub.3                                                               6-Cl        O     O                                             SO.sub.2 N(CH.sub.3).sub.2                                                                  H           O     O                                             SO.sub.2 N(C.sub.2 H.sub.5).sub.2                                                           H           O     O                                              ##STR162##   H           O     O                                             CO.sub.2 CH.sub.3                                                                           H           S     O                                             CO.sub.2 CH(CH.sub.3).sub.2                                                                 H           S     O                                             CO.sub.2 CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3                                               H           S     O                                             CO.sub.2 CH.sub.2 CHCHCH.sub.3                                                              H           S     O                                             CON(OCH.sub.3)CH.sub.3                                                                      H           S     O                                              ##STR163##   H           S     O                                             SO.sub.2 N(C.sub.2 H.sub.5).sub.2                                                           H           S     O                                              ##STR164##   H           S     O                                             CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                H           O     O    128-131°                          CO.sub.2 CH(CH.sub.3).sub.2                                                                 H           O     O    169-171°                          CO.sub.2 CH.sub.2 CHCH.sub.2                                                                H           O     O    156-159°                          Cl            H           O     O    193-195°                          CO.sub.2 CH.sub.3                                                                           5-F         S     O                                             CO.sub.2 CH.sub.3                                                                           5-OCH.sub.3 S     O                                             CON(CH.sub.3).sub.2                                                                         6-Cl        S     O                                             SO.sub.2 N(OCH.sub.3)CH.sub.3                                                               3-Cl        S     O                                              ##STR165##   4-CH.sub.3  S     O                                             ______________________________________                                    

                  TABLE 1-E                                                       ______________________________________                                         ##STR166##                                                                    R.sub.2        R.sub.3  W      Y    m.p.                                     ______________________________________                                        CO.sub.2 CH.sub.3                                                                             H        O      CH.sub.2                                      CO.sub.2 CH.sub.3                                                                             4-CH.sub.3 O                                                                           O      CH.sub.2                                      CO.sub.2 C.sub.2 H.sub.5                                                                      H        O      CH.sub.2                                      CO.sub.2 C.sub.2 H.sub.5                                                                      Cl       O      CH.sub.2                                      CO.sub.2 CH(CH.sub.3).sub.2                                                                   H        O      CH.sub.2                                      CO.sub.2 CH.sub.2CHCH.sub.2                                                                   H        O      CH.sub.2                                      CO.sub.2 CH.sub.2 CHCHCH.sub.2 CH.sub.3                                                       5-Br     O      CH.sub.2                                       ##STR167##     H        O      CH.sub.2                                       ##STR168##     H        O      CH.sub.2                                      CO.sub.2 (CH.sub.2 CH.sub.2).sub.2 OC.sub.2 H.sub.5                                           H        O      CH.sub.2                                      CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 OC.sub.2 H.sub.5                                          H        O      CH.sub.2                                      CON(CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3).sub.2                                                H        O      CH.sub.2                                       ##STR169##     H        O      CH.sub.2                                      COSCH.sub.3     H        O      CH.sub.2                                       ##STR170##     H        O      CH.sub.2                                      COSCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                        3-Cl     O      CH.sub.2                                      SO.sub.2 N(CH.sub.3).sub.2                                                                    H        O      CH.sub.2                                      SO.sub.2 N(C.sub.2 H.sub.5).sub.2                                                             H        O      CH.sub.2                                       ##STR171##     H        O      CH.sub.2                                      CO.sub.2 CH.sub.3                                                                             H        O      O    206-210°                          CO.sub.2 CH.sub.3                                                                             4-CH.sub.3 O                                                                           O      O                                             CO.sub.2 C.sub.2 H.sub.5                                                                      H        O      O                                             CO.sub.2 C.sub.2 H.sub.5                                                                      Cl       O      O                                             CO.sub.2 CH(CH.sub.3).sub.2                                                                   H        O      O                                             CO.sub.2 CH.sub.2CHCH.sub.2                                                                   H        O      O    155-157°                          CO.sub.2 CH.sub.2 CHCHCH.sub.2 CH.sub.3                                                       5-Br     O      O                                              ##STR172##     H        O      O                                              ##STR173##     H        O      O                                             CO.sub.2 (CH.sub.2 CH.sub.2).sub.2 OC.sub.2 H.sub.5                                           H        O      O                                             CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 OC.sub.2 H.sub.5                                          H        O      O                                             CON(CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3).sub.2                                                H        O      O                                              ##STR174##     H        O      O                                             COSCH.sub.3     H        O      O                                              ##STR175##     H        O      O                                             COSCH.sub.2 CH.sub.2 CH.sub.3                                                                 6-CH.sub.3                                                                             O      O                                              ##STR176##     3-F      O      O                                             SO.sub.2 N(CH.sub.3).sub.2                                                                    H        O      O                                             SO.sub.2 N(C.sub.2 H.sub.5).sub.2                                                             H        O      O                                              ##STR177##     H        O      O                                             CO.sub.2 CH.sub.2 CH.sub.3                                                                    H        S      O                                             CO.sub.2 CH(CH.sub.3).sub.2                                                                   H        S      O                                             CO.sub.2 CH.sub.2 CH.sub.2 Br                                                                 H        S      O                                             CO.sub.2 CH.sub.2 CHCH.sub.2                                                                  H        S      O                                             CO.sub.2 (CH.sub.2 CH.sub.2 O).sub.2 CH.sub.3                                                 H        S      O                                             CON[CH(CH.sub.3).sub.2 ].sub.2                                                                H        S      O                                             SO.sub.2 N(OCH.sub.3)CH.sub.3                                                                 H        S      O                                             CO.sub.2 CH.sub.3                                                                             6-CH.sub.3                                                                             S      O                                             CO.sub.2 CH(CH.sub.3).sub.2                                                                   5-Cl     S      O                                             CON(OCH.sub.3)CH.sub.3                                                                        5-OCH.sub.3                                                                            S      O                                             SO.sub.2 N(CH.sub.3).sub.2                                                                    4-F      S      O                                              ##STR178##     3-Br     S      O                                             CH.sub.3        H        O      O    226-228°                          CO.sub.2 CH(CH.sub.3).sub.2                                                                   H        O      O    214-216°                          NO.sub.2        H        O      O    203-206°                          ______________________________________                                    

The compounds in Table II are prepared by reactingpyridinesulfonylisocyanates or pyridinesulfonylisothiocyanates with theappropriate 2-amino-pyrimidine as illustrated by Examples 6 and 7.

EXAMPLE 6 2-Chloro-3-pyridinesulfonylisocyanate

To 125 ml of dry xylene were added with stirring 20.7 g of2-chloro-N-(butylcarbamoyl)-3-pyridinesulfonamide. This solution washeated to reflux, and phosgene added until no further uptake of this gaswas observed. It was then cooled, filtered and the solvent was removedin vacuo to yield 2-chloro-3-pyridinesulfonylisocyanate as an oil Bp108°-110° (0.7 mm Hg). This product showed a sharp absorption peak inthe infrared region at 2220 cm⁻¹.

EXAMPLE 72-Chloro-N-[(6,7-dihydro-4-methyl-5H-cyclopentapyrimidin-2-yl)aminocarbonyl]pyridine-3-sulfonamide

To a dry, stirred solution of 7.5 g of6,7-dihydro-4-methyl-5H-cyclopentapyrimidin-2-amine in 200 ml ofmethylene chloride at ambient temperature and pressure is added 13 g of2-chloropyrimidine-3-sulfonylisocyanate. The resulting mixture isstirred at reflux for 2 hours and then concentrated at reduced pressure.The residue is triturated with 1-chlorobutane and filtered to yield thedesired solid product.

                  TABLE II-A                                                      ______________________________________                                         ##STR179##                                                                    R.sub.4              W        Y                                              ______________________________________                                        2-F                   O        CH.sub.2                                       2-Br                  O        CH.sub.2                                       2-CH.sub.3            O        CH.sub.2                                       2-OCH.sub.3           O        CH.sub.2                                       2-NO.sub.2            O        CH.sub.2                                       2-CO.sub.2 CH.sub.3   O        CH.sub.2                                       2-CO.sub.2 CH(CH.sub.3).sub.2                                                                       O        CH.sub.2                                        ##STR180##           O        CH.sub.2                                       2-SCH.sub.3           O        CH.sub.2                                       4-Cl                  O        CH.sub.2                                       4-F                   O        CH.sub.2                                       4-Br                  O        CH.sub.2                                       4-C.sub.2 H.sub.5     O        CH.sub.2                                       4-CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                               O        CH.sub.2                                       4-OCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                              O        CH.sub.2                                       4-NO.sub.2            O        CH.sub.2                                       4-CO.sub.2 C.sub.2 H.sub.5                                                                          O        CH.sub.2                                       4-CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                               O        CH.sub.2                                       4-CO.sub.2 CH.sub.2 CH(CH.sub.3 ).sub.2                                                             O        CH.sub.2                                       4-CO.sub.2 (CH.sub.2).sub.4 CH.sub.3                                                                O        CH.sub.2                                       4-CO.sub.2 (CH.sub.2).sub.5 CH.sub.3                                                                O        CH.sub.2                                       4-SCH.sub.3           O        CH.sub.2                                       H                     O        CH.sub.2                                       2-S(CH.sub.2).sub.3 CH.sub.3                                                                        O        CH.sub.2                                       2-F                   O        O                                              2-Br                  O        O                                              2-CH.sub.3            O        O                                              2-OCH.sub.3           O        O                                              2-NO.sub.2            O        O                                              2-CO.sub.2 CH.sub.3   O        O                                              2-CO.sub.2 CH(CH.sub.3).sub.2                                                                       O        O                                               ##STR181##           O        O                                              2-SCH.sub.3           O        O                                              4-Cl                  O        O                                              4-F                   O        O                                              4-Br                  O        O                                              4-C.sub.2 H.sub.5     O        O                                              4-CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                               O        O                                              4-OCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                              O        O                                              4-NO.sub.2            O        O                                              4-CO.sub.2 C.sub.2 H.sub.5                                                                          O        O                                              4-CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                               O        O                                              4-CO.sub.2 CH.sub.2 CH(CH.sub.3).sub.2                                                              O        O                                              4-CO.sub.2 (CH.sub.2).sub.4 CH.sub.3                                                                O        O                                              4-CO.sub.2 (CH.sub.2).sub.5 CH.sub.3                                                                O        O                                              4-SCH.sub.3           O        O                                              2-Cl                  O        O                                              2-S(CH.sub.2).sub.3 CH.sub.3                                                                        O        O                                              H                     S        O                                              2-Cl                  S        O                                              2-Br                  S        O                                              2-CH.sub.3            S        O                                              2-OCH.sub.3           S        O                                              2-CO.sub.2 CH(CH.sub.3).sub.2                                                                       S        O                                              2-SCH.sub.3           S        O                                              4-Cl                  S        O                                              4-F                   S        O                                              4-C.sub.2 H.sub.5     S        O                                              4-OCH(CH.sub.3).sub.2 S        O                                              4-NO.sub.2            S        O                                              4-CO.sub.2 CH.sub.3   S        O                                              ______________________________________                                    

                  TABLE II-B                                                      ______________________________________                                         ##STR182##                                                                    R.sub.4             W         Y                                              ______________________________________                                        2-Br                 O         CH.sub.2                                       2-CH.sub.3           O         CH.sub.2                                        ##STR183##          O         CH.sub.2                                       2-CH.sub.2 CH.sub.2 CH.sub.3                                                                       O         CH.sub.2                                       2-OCH.sub.3          O         CH.sub.2                                       2-NO.sub.2           O         CH.sub.2                                       2-CO.sub.2 CH.sub.3  O         CH.sub.2                                       2-CO.sub.2 (CH.sub.2).sub.5 CH.sub.3                                                               O         CH.sub.2                                       2-CO.sub.2 CH.sub.2 CH.sub.3                                                                       O         CH.sub.2                                       4-Cl                 O         CH.sub.2                                       4-F                  O         CH.sub.2                                       4-Br                 O         CH.sub.2                                       4-CH.sub.3           O         CH.sub.2                                       4-C.sub.2 H.sub.5    O         CH.sub.2                                       4-CH(CH.sub.3).sub.2 O         CH.sub.2                                       4-OCH.sub.3          O         CH.sub.2                                       4-NO.sub.2           O         CH.sub.2                                       4-CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                     O         CH.sub. 2                                      4-CO.sub.2 CH(CH.sub.3).sub.2                                                                      O         CH.sub.2                                       4-SCH.sub.3          O         CH.sub.2                                       2-Cl                 O         CH.sub.2                                       2-F                  O         CH.sub.2                                       2-OCH.sub.2 CH.sub.2 CH.sub.3                                                                      O         CH.sub.2                                       2-OCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                             O         CH.sub.2                                       H                    O         CH.sub.2                                       2-Br                 O         O                                              2-CH.sub.3           O         O                                               ##STR184##          O         O                                              2-CH.sub.2 CH.sub.2 CH.sub.3                                                                       O         O                                              2-OCH.sub.3          O         O                                              2-NO.sub.2           O         O                                              2-CO.sub.2 CH.sub.3  O         O                                              2-CO.sub.2 (CH.sub.2).sub.5 CH.sub.3                                                               O         O                                              2-CO.sub.2 CH.sub.2 CH.sub.3                                                                       O         O                                              4-Cl                 O         O                                              4-F                  O         O                                              4-Br                 O         O                                              4-CH.sub.3           O         O                                              4-C.sub.2 H.sub.5    O         O                                              4-CH(CH.sub.3).sub.2 O         O                                              4-OCH.sub.3          O         O                                              4-NO.sub.2           O         O                                              4-CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                     O         O                                              4-CO.sub.2 CH(CH.sub.3).sub.2                                                                      O         O                                              4-SCH.sub.3          O         O                                              2-Cl                 O         O                                              2-F                  O         O                                              2-OCH.sub.2 CH.sub.2 CH.sub.3                                                                      O         O                                              2-OCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                             O         O                                              H                    O         O                                              H                    S         O                                              2-Cl                 S         O                                              2-Br                 S         O                                              2-F                  S         O                                              2-CH.sub.3           S         O                                              2-OCH.sub.3          S         O                                              2-NO.sub.2           S         O                                              2-CO.sub.2 CH.sub.3  S         O                                              4-Cl                 S         O                                              4-F                  S         O                                              4-C.sub.2 H.sub.5    S         O                                              4-NO.sub.2           S         O                                              4-CO.sub.2 C.sub.2 H.sub.5                                                                         S         O                                              ______________________________________                                    

                  TABLE II-C                                                      ______________________________________                                         ##STR185##                                                                    R.sub.4             W         Y                                              ______________________________________                                        2-Br                 O         CH.sub.2                                       2-CH.sub.3           O         CH.sub.2                                        ##STR186##          O         CH.sub.2                                       2-CH.sub.2 CH.sub.2 CH.sub.3                                                                       O         CH.sub.2                                       2-OCH.sub.3          O         CH.sub.2                                       2-NO.sub.2           O         CH.sub.2                                       2-CO.sub.2 CH.sub.3  O         CH.sub.2                                       2-CO.sub.2 (CH.sub.2).sub.5 CH.sub.3                                                               O         CH.sub.2                                       2-CO.sub.2 CH.sub.2 CH.sub.3                                                                       O         CH.sub.2                                       4-Cl                 O         CH.sub.2                                       4-F                  O         CH.sub.2                                       4-Br                 O         CH.sub.2                                       4-CH.sub.3           O         CH.sub.2                                       4-C.sub.2 H.sub.5    O         CH.sub.2                                       4-CH(CH.sub.3).sub.2 O         CH.sub.2                                       4-OCH.sub.3          O         CH.sub.2                                       4-NO.sub.2           O         CH.sub.2                                       4-CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                     O         CH.sub.2                                       4-CO.sub. 2 CH(CH.sub.3).sub.2                                                                     O         CH.sub.2                                       4-SCH.sub.3          O         CH.sub.2                                       2-Cl                 O         CH.sub.2                                       2-F                  O         CH.sub.2                                       2-OCH.sub.2 CH.sub.2 CH.sub.3                                                                      O         CH.sub.2                                       2-OCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                             O         CH.sub.2                                       H                    O         CH.sub.2                                       2-S(CH.sub.2).sub.2 CH.sub.3                                                                       O         CH.sub.2                                       2-Br                 O         O                                              2-CH.sub.3           O         O                                               ##STR187##          O         O                                              2-CH.sub.2 CH.sub.2 CH.sub.3                                                                       O         O                                              2-OCH.sub.3          O         O                                              2-NO.sub.2           O         O                                              2-CO.sub.2 CH.sub.3  O         O                                              2-CO.sub.2 (CH.sub.2).sub.5 CH.sub.3                                                               O         O                                              2-CO.sub.2 CH.sub.2 CH.sub.3                                                                       O         O                                              4-Cl                 O         O                                              4-F                  O         O                                              4-Br                 O         O                                              4-CH.sub.3           O         O                                              4-C.sub.2 H.sub.5    O         O                                              4-CH(CH.sub.3).sub.2 O         O                                              4-OCH.sub.3          O         O                                              4-NO.sub.2           O         O                                              4-CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                     O         O                                              4-CO.sub.2 CH(CH.sub.3).sub.2                                                                      O         O                                              4-SCH.sub.3          O         O                                              2-Cl                 O         O                                              2-F                  O         O                                              2-OCH.sub.2 CH.sub.2 CH.sub.3                                                                      O         O                                              2-OCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                             O         O                                              H                    O         O                                              2-S(CH.sub.2 ).sub.2 CH.sub.3                                                                      O         O                                              2-Cl                 S         O                                              2-Br                 S         O                                              2-CH.sub.3           S         O                                              2-OCH.sub.3          S         O                                              2-NO.sub.2           S         O                                              2-CO.sub.2 CH(CH.sub.3).sub.2                                                                      S         O                                              2-SCH.sub.3          S         O                                              4-Cl                 S         O                                              4-F                  S         O                                              4-CH.sub.3           S         O                                              4-OCH.sub.3          S         O                                              4-CO.sub.2 CH.sub.3  S         O                                              ______________________________________                                    

                  TABLE II-D                                                      ______________________________________                                         ##STR188##                                                                   R.sub.4          W            Y                                               ______________________________________                                        2-Cl             O            CH.sub.2                                        2-F              O            CH.sub.2                                        2-Br             O            CH.sub.2                                        2-CH.sub.3       O            CH.sub.2                                        2-CH.sub.2 CH.sub.2 CH.sub.3                                                                   O            CH.sub.2                                        2-NO.sub.2       O            CH.sub.2                                        2-CO.sub.2 CH.sub.3                                                                            O            CH.sub.2                                        2-CO.sub.2 CH.sub.2 CH(CH.sub.3).sub.2                                                         O            CH.sub.2                                        2-SCH.sub.3      O            CH.sub.2                                        4-Cl             O            CH.sub.2                                        4-F              O            CH.sub.2                                        4-CH.sub.2 CH.sub.2 CH.sub.3                                                                   O            CH.sub.2                                        4-CH.sub.3       O            CH.sub.2                                        4-CH.sub.3 O     O            CH.sub.2                                        4-NO.sub.2       O            CH.sub.2                                        4-CO.sub.2 CH(CH.sub.3).sub.2                                                                  O            CH.sub.2                                        4-SCH.sub.3      O            CH.sub.2                                        2-S(CH.sub.2).sub.3 CH.sub.3                                                                   O            CH.sub.2                                        2-Cl             O            O                                               2-F              O            O                                               2-Br             O            O                                               2-CH.sub.3       O            O                                               2-CH.sub.2 CH.sub. 2 CH.sub.3                                                                  O            O                                               2-NO.sub.2       O            O                                               2-CO.sub.2 CH.sub.3                                                                            O            O                                               2-CO.sub.2 CH.sub.2 CH(CH.sub.3).sub.2                                                         O            O                                               2-SCH.sub.3      O            O                                               4-Cl             O            O                                               4-F              O            O                                               4-CH.sub.2 CH.sub.2 CH.sub.3                                                                   O            O                                               4-CH.sub.3       O            O                                               4-CH.sub.3 O     O            O                                               4-NO.sub.2       O            O                                               4-CO.sub.2 CH(CH.sub.3).sub.2                                                                  O            O                                               4-SCH.sub.3      O            O                                               2-S(CH.sub.2).sub.3 CH.sub.3                                                                   O            O                                               2-Cl             S            O                                               2-F              S            O                                               2-Br             S            O                                               2-C.sub.2 H.sub.5                                                                              S            O                                               2-OC.sub.2 H.sub.5                                                                             S            O                                               2-NO.sub.2       S            O                                               2-CH.sub.2 CH.sub.3                                                                            S            O                                               2-SCH(CH.sub.3).sub.2                                                                          S            O                                               4-Cl             S            O                                               4-F              S            O                                               4-CH.sub.3       S            O                                               4-OCH.sub.3      S            O                                               4-NO.sub.2       S            O                                               4-CO.sub.2 CH.sub.3                                                                            S            O                                               ______________________________________                                    

                  TABLE II-E                                                      ______________________________________                                         ##STR189##                                                                   R.sub.4        W              Y                                               ______________________________________                                        4-Cl           O              CH.sub.2                                        4-Br           O              CH.sub.2                                        4-CH.sub.3     O              CH.sub.2                                        4-OCH.sub.3    O              CH.sub.2                                        4-NO.sub.2     O              CH.sub.2                                        4-CO.sub.2 CH.sub.3                                                                          O              CH.sub.2                                        4-CO.sub.2 (CH.sub.2).sub.4 CH.sub.3                                                         O              CH.sub.2                                        4-SCH.sub.3    O              CH.sub.2                                        2-Cl           O              CH.sub.2                                        2-F            O              CH.sub.2                                        2-Br           O              CH.sub.2                                        2-CH(CH.sub.3).sub.2                                                                         O              CH.sub.2                                        2-CH.sub.3 O   O              CH.sub.2                                        2-NO.sub.2     O              CH.sub.2                                        2-COOC.sub.2 H.sub.5                                                                         O              CH.sub.2                                        2-SCH.sub.3    O              CH.sub.2                                        4-SCH.sub.2 CH.sub.3                                                                         O              CH.sub.2                                        4-Cl           O              O                                               4-Br           O              O                                               4-CH.sub.3     O              O                                               4-OCH.sub.3    O              O                                               4-NO.sub.2     O              O                                               4-CO.sub.2 CH.sub.3                                                                          O              O                                               4-CO.sub.2 (CH.sub.2).sub.4 CH.sub. 3                                                        O              O                                               4-SCH.sub.3    O              O                                               2-Cl           O              O                                               2-F            O              O                                               2-Br           O              O                                               2-CH(CH.sub.3).sub.2                                                                         O              O                                               2-CH.sub.3 O   O              O                                               2-NO.sub.2     O              O                                               2-COOC.sub.2 H.sub.5                                                                         O              O                                               2-SCH.sub.3    O              O                                               4-SCH.sub.2 CH.sub.3                                                                         O              O                                               2-Cl           S              O                                               2-F            S              O                                               2-Br           S              O                                               2-C.sub.2 H.sub.5                                                                            S              O                                               2-OCH(CH.sub.3).sub.2                                                                        S              O                                               2-NO.sub.2     S              O                                               2-CO.sub.2 CH.sub.3                                                                          S              O                                               2-SCH.sub.3    S              O                                               4-Cl           S              O                                               4-Br           S              O                                               4-CH.sub.3     S              O                                               4-OCH.sub.3    S              O                                               4-NO.sub.2     S              O                                               4-CO.sub.2 CH.sub.3                                                                          S              O                                               ______________________________________                                    

EXAMPLE 82-Isopropylaminocarbonyl-N-[(6,7-dihydro-4-methyl-5H-cyclopentapyrimidin-2-yl)aminocarbonyl]benzenesulfonamide

To 21.2 ml of 25% trimethylaluminum in hexane (2.36 molar) undernitrogen is added 2.9 g of isopropyl amine in 100 ml of dried methylenechloride. The mixture is stirred at ambient temperature until evolutionof methane gas ceases and then 19.5 g of methyl2[[(6,7-dihydro-4-methyl-5H-cyclopentapyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzoateand 200 ml of dry toluene is added. The resulting mixture is heated todistill off the methylene chloride and hexane, after which heating iscontinued at the reflux temperature of toluene. After 2 hours, thetoluene is removed in vacuo, and 200 ml of methylene chloride and 100 mlof 10% hydrochloric acid are added. The phases are separated, and themethylene chloride phase is washed once with water, dried over magnesiumsulfate, and filtered, and the methylene chloride distilled to yield thedesired compound.

By using the procedure of Example 8 with an equivalent amount of anappropriately substituted benzoic acid ester andalkylaminodialkylaluminum, the compounds of Table III can be prepared.

                  TABLE III-A                                                     ______________________________________                                         ##STR190##                                                                   R.sub.3                                                                            R.sub.9      R.sub.8    W   X     Y    m.p.                              ______________________________________                                        H    CH.sub.3     H          O   CH.sub.3                                                                            CH.sub.2                               H    C.sub.2 H.sub.5                                                                            H          O   CH.sub.3                                                                            CH.sub.2                               H    CH(CH.sub.3).sub.2                                                                         H          O   CH.sub.3                                                                            CH.sub.2                               5-Cl CH.sub.3     H          O   CH.sub.3                                                                            CH.sub.2                               6-Cl CH(CH.sub.3).sub.2                                                                         H          O   CH.sub.3                                                                            CH.sub.2                               H    CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                        H          O   CH.sub.3                                                                            CH.sub.2                               H    CH(CH.sub.3).sub.2                                                                         H          O   OCH.sub.3                                                                           CH.sub.2                               5-Cl C.sub.2 H.sub.5                                                                            H          O   OCH.sub.3                                                                           CH.sub.2                               6-Cl CH.sub.2 CH.sub.2 CH.sub.3                                                                 H          O   OCH.sub.3                                                                           CH.sub.2                               H    CH(CH.sub.3).sub.2                                                                         CH.sub.3   O   CH.sub.3                                                                            CH.sub.2                               H    C.sub.2 H.sub.5                                                                            C.sub.2 H.sub.5                                                                          O   CH.sub.3                                                                            CH.sub.2                                                                           166-                                                                          169°                       H    CH(CH.sub.3).sub.2                                                                         CH(CH.sub.3).sub.2                                                                       O   CH.sub.3                                                                            CH.sub.2                               H    (CH.sub.2).sub.4 H                                                                         (CH.sub.2).sub.4 H                                                                       O   CH.sub.3                                                                            CH.sub.2                               H    H            H          O   CH.sub.3                                                                            CH.sub.2                               H    CH.sub.3     H          O   H     CH.sub.2                               5-Cl C.sub.2 H.sub.5                                                                            H          O   H     CH.sub.2                               6-Cl CH(CH.sub.3).sub.2                                                                         H          O   H     CH.sub.2                               H    CH.sub.2 CH.sub.2 CH.sub.3                                                                 CH.sub.3   O   H     CH.sub.2                               H    C.sub.2 H.sub.5                                                                            C.sub.2 H.sub.5                                                                          O   H     CH.sub.2                               H    H            H          O   H     CH.sub.2                               H    CH.sub.3     CH.sub.3   O   Cl    CH.sub.2                               H    C.sub.2 H.sub.5                                                                            H          O   Cl    CH.sub.2                               H    CH(CH.sub.3).sub.2                                                                         H          O   Cl    CH.sub.2                               H    CH.sub.3     H          O   Cl    CH.sub.2                               5-Cl CH.sub.3     CH.sub.3   O   OC.sub.2 H.sub.5                                                                    CH.sub.2                               6-Cl C.sub.2 H.sub.5                                                                            C.sub.2 H.sub.5                                                                          O   OC.sub.2 H.sub.5                                                                    CH.sub.2                               H    CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2                                                      O     OC.sub.2 H.sub.5                                                                    CH.sub.2                                 H    CH.sub.3     H          O   CH.sub.3                                                                            O                                      H    C.sub.2 H.sub.5                                                                            H          O   CH.sub.3                                                                            O                                      H    CH(CH.sub.3).sub.2                                                                         H          O   CH.sub.3                                                                            O                                      5-Cl CH.sub.3     H          O   CH.sub.3                                                                            O                                      6-Cl CH(CH.sub.3).sub.2                                                                         H          O   CH.sub.3                                                                            O                                      H    CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                        H          O   CH.sub.3                                                                            O                                      H    CH(CH.sub.3).sub.2                                                                         H          O   OCH.sub.3                                                                           O                                      5-Cl C.sub.2 H.sub.5                                                                            H          O   OCH.sub.3                                                                           O                                      6-Cl CH.sub.2 CH.sub.2 CH.sub.3                                                                 H          O   OCH.sub.3                                                                           O                                      H    CH(CH.sub.3).sub.2                                                                         CH.sub.3   O   CH.sub.3                                                                            O                                      H    C.sub.2 H.sub.5                                                                            C.sub.2 H.sub.5                                                                          O   CH.sub.3                                                                            O                                      H    CH(CH.sub.3).sub.2                                                                         CH(CH.sub.3).sub.2                                                                       O   CH.sub.3                                                                            O                                      H    (CH.sub.2).sub.4 H                                                                         (CH.sub.2).sub.4 H                                                                       O   CH.sub.3                                                                            O                                      H    H            H          O   CH.sub.3                                                                            O                                      H    CH.sub.3     H          O   H     O                                      5-Cl CH.sub.3     H          O   H     O                                      6-Cl C.sub.2 H.sub.5                                                                            H          O   H     O                                      H    CH.sub.2 CH.sub.2 CH.sub.3                                                                 CH.sub.3   O   H     O                                      H    CH(CH.sub.3).sub.2                                                                         C.sub.2 H.sub.5                                                                          O   H     O                                      H    (CH.sub.2).sub.4 H                                                                         CH.sub.3   O   H     O                                      H    H            H          O   H     O                                      H    CH.sub.3     CH.sub.3   O   Cl    O                                      H    C.sub.2 H.sub.5                                                                            H          O   Cl    O                                      H    CH(CH.sub.3).sub.2                                                                         H          O   Cl    O                                      H    CH.sub.3     H          O   Cl    O                                      5-Cl CH.sub.3     CH.sub.3   O   OC.sub.2 H.sub.5                                                                    O                                      6-Cl C.sub.2 H.sub.5                                                                            C.sub.2 H.sub.5                                                                          O   OC.sub.2 H.sub.5                                                                    O                                      H    CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2                                                      O     OC.sub.2 H.sub.5                                                                    O                                        H    H            H          S   CH.sub.3                                                                            O                                      H    CH.sub.3     H          S   CH.sub.3                                                                            O                                      H    CH(CH.sub.3).sub.2                                                                         H          S   CH.sub.3                                                                            O                                            ##STR191##  H          S   CH.sub.3                                                                            O                                      H    CH.sub.3     CH.sub.3   S   CH.sub.3                                                                            O                                      H    CH(CH.sub.3).sub.2                                                                         CH(CH.sub.3).sub.2                                                                       S   CH.sub.3                                                                            O                                      5-Cl C.sub.2 H.sub.5                                                                            H          S   CH.sub.3                                                                            O                                      6-Cl CH.sub.3     CH.sub.3   S   CH.sub.3                                                                            O                                      H    H            H          S   OCH.sub.3                                                                           O                                      H    CH.sub.3     H          S   OCH.sub.3                                                                           O                                      H    CH.sub.3     CH.sub.3   S   OCH.sub.3                                                                           O                                      5-Cl CH.sub.3     CH.sub.3   S   OCH.sub.3                                                                           O                                      H    CH.sub.3     H          S   H     O                                      H    CH.sub.3     C.sub.2 H.sub.5                                                                          S   H     O                                      H    CH(CH.sub.3).sub.2                                                                         CH(CH.sub.3).sub.2                                                                       S   H     O                                      H    CH.sub.3     H          S   Cl    O                                      H    CH.sub.3     CH.sub.3   S   Cl    O                                      6-Cl CH.sub.2 CH.sub.2 CH.sub.3                                                                 H          S   Cl    O                                      H    CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2                                                               S     Cl    O                                        H    H            H          S   OC.sub.2 H.sub.5                                                                    O                                      H    CH.sub.3     CH.sub.3   S   OC.sub.2 H.sub.5                                                                    O                                      5-Cl CH.sub.3     H          S   OC.sub.2 H.sub.5                                                                    O                                      H    CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2                                                              S     OC.sub.2 H.sub.5                                                                    O                                        H    H            H          S   CH.sub.3                                                                            O                                      H    CH.sub.3     H          S   CH.sub.3                                                                            O                                      H    C.sub.2 H.sub. 5                                                                           H          S   CH.sub.3                                                                            O                                      H    CH.sub.3     CH.sub.3   S   CH.sub.3                                                                            O                                      H    CH.sub.3     C.sub.2 H.sub.5                                                                          S   CH.sub.3                                                                            O                                      6-Cl CH(CH.sub.3).sub.2                                                                         H          S   CH.sub.3                                                                            O                                      5-Cl CH.sub.3     CH.sub.3   S   CH.sub.3                                                                            O                                      H    H            H          S   OCH.sub.3                                                                           O                                      H    CH.sub.3     H          S   OCH.sub.3                                                                           O                                      H    C.sub.2 H.sub.5                                                                            C.sub.2 H.sub.5                                                                          S   OCH.sub.3                                                                           O                                      5-Cl CH.sub.3     CH(CH.sub.3).sub.2                                                                       S   OCH.sub.3                                                                           O                                      H    CH.sub.3     H          S   H     O                                      H    (CH.sub.2).sub.3 CH.sub.3                                                                  H          S   H     O                                      H    CH.sub.3     CH.sub.3   S   H     O                                      H    C.sub.2 H.sub.5                                                                            H          S   Cl    O                                      H    C.sub.2 H.sub.5                                                                            CH.sub.3   S   Cl    O                                      H    CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2                                                      S     Cl    O                                        5-Cl                                                                                ##STR192##  H          S   Cl    O                                      H    H            H          S   OC.sub.2 H.sub.5                                                                    O                                      H    CH.sub.3     CH.sub.3   S   OC.sub.2 H.sub.5                                                                    O                                      H    CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2                                                              S     OC.sub.2 H.sub.5                                                                    O                                        H    CH(CH.sub.3).sub.2                                                                         CH.sub.3   S   OC.sub.2 H.sub.5                                                                    O                                      6-Cl C.sub.2 H.sub.5                                                                            C.sub.2 H.sub.5                                                                          S   OC.sub.2 H.sub.5                                                                    O                                      ______________________________________                                    

                  TABLE III-B                                                     ______________________________________                                         ##STR193##                                                                   R.sub.3                                                                             R.sub.9     R.sub.8     W    X      Y                                   ______________________________________                                        H     C.sub.2 H.sub.5                                                                           H           O    CH.sub.3                                                                             CH.sub.2                            H     CH(CH.sub.3).sub.2                                                                        H           O    CH.sub.3                                                                             CH.sub.2                            H     CH.sub.2 CH.sub.2 CH.sub.3                                                                H           O    CH.sub.3                                                                             CH.sub.2                            5-Cl                                                                                 ##STR194## H           O    CH.sub.3                                                                             CH.sub.2                            H     CH.sub.3    CH.sub.3    O    CH.sub.3                                                                             CH.sub.2                            H     C.sub.2 H.sub.5                                                                           CH.sub.3    O    CH.sub.3                                                                             CH.sub.2                            H     C.sub.2 H.sub.5                                                                           C.sub.2 H.sub.5                                                                           O    CH.sub.3                                                                             CH.sub.2                            H     H           H           O    CH.sub.3                                                                             CH.sub.2                            H     C.sub.2 H.sub.5                                                                           H           O    CH.sub.3                                                                             O                                   H     CH(CH.sub.3).sub.2                                                                        H           O    CH.sub.3                                                                             O                                   H     CH.sub.2 CH.sub.2 CH.sub.3                                                                H           O    CH.sub.3                                                                             O                                   5-Cl                                                                                 ##STR195## H           O    CH.sub.3                                                                             O                                   H     CH.sub.3    CH.sub.3    O    CH.sub.3                                                                             O                                   H     C.sub.2 H.sub.5                                                                           CH.sub.3    O    CH.sub.3                                                                             O                                   H     C.sub.2 H.sub.5                                                                           C.sub.2 H.sub.5                                                                           O    CH.sub.3                                                                             O                                   H     H           H           O    CH.sub.3                                                                             O                                   H     C.sub.2 H.sub.5                                                                           CH.sub.3    O    OCH.sub.3                                                                            CH.sub.2                            H     CH(CH.sub.3).sub.2                                                                        H           O    OCH.sub.3                                                                            CH.sub.2                            H     CH.sub.3    CH.sub.3    O    OCH.sub.3                                                                            O                                   H     C.sub.2 H.sub.5                                                                           C.sub.2 H.sub.5                                                                           O    OCH.sub.3                                                                            O                                   H     CH.sub.3    H           S    CH.sub.3                                                                             O                                   H     CH.sub.2 CH.sub.2 CH.sub.3                                                                H           S    CH.sub.3                                                                             O                                   H     CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2                                                               S      CH.sub.3                                                                             O                                     5-Cl  CH.sub.3    CH.sub.3    S    CH.sub.3                                                                             O                                   H     C.sub.2 H.sub.5                                                                           CH.sub.3    S    CH.sub.3                                                                             O                                   H     C.sub.2 H.sub.5                                                                           H           S    OCH.sub.3                                                                            O                                   H     CH.sub.2 (CH.sub.3).sub.3                                                                 H           S    OCH.sub.3                                                                            O                                   H     CH.sub.3    CH.sub.3    S    OCH.sub.3                                                                            O                                   H     CH.sub.3    CH.sub.2 CH.sub.2 CH.sub.3                                                                S    OCH.sub.3                                                                            O                                   6-Cl  CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2                                                      S      OCH.sub.3                                                                            O                                     ______________________________________                                    

By using the procedures described above and the appropriate reactantsand 4-chloro or 4-ethoxy-5,6-dihydrofuro[2,3-d]pyrimidin-2-amine or4-chloro or 4-ethoxy-6,7-dihydro-5H-cyclopentapyrimidin-2-amine, thecompounds of Table IV-A can be prepared.

Similarly, compounds of Table IV-B can be prepared using the appropriatereactants and starting from6,7-dihydro-5H-pyrano[2,3-d]pyrimidin-2-amine substituted in the4-position with hydrogen, chlorine or ethoxy.

                                      TABLE IV-A                                  __________________________________________________________________________     ##STR196##                                                                    ##STR197##                                                                   R.sub.2   R.sub.3                                                                            R.sub.4  W  X   Y  m.p.                                        __________________________________________________________________________    H         H    --       O  Cl  O                                              CO.sub.2 CH.sub.3                                                                       H    --       O  Cl  O  215-219°                             CO.sub.2 CH.sub.3                                                                       5-Cl --       O  Cl  CH.sub.2                                       SO.sub.2 N(CH.sub.3).sub.2                                                              H    --       O  OC.sub.2 H.sub.5                                                                  CH.sub.2                                       Cl        H    --       O  OC.sub.2 H.sub.5                                                                  O                                              NO.sub.2  H    --       O  OC.sub.2 H.sub.5                                                                  CH.sub.2                                       SO.sub.2 CH.sub.3                                                                       H    --       O  OC.sub.2 H.sub.5                                                                  CH.sub.2                                       CO.sub.2 CH.sub. 2 CHCH.sub.2                                                           H    --       O  OC.sub.2 H.sub.5                                                                  O                                              CON(CH.sub.3).sub.2                                                                     H    --       O  OC.sub.2 H.sub.5                                                                  CH.sub.2                                        ##STR198##                                                                             H    --       O  OC.sub.2 H.sub.5                                                                  O                                              F         H    --       O  OC.sub.2 H.sub.5                                                                  O                                              --        --   2-CO.sub.2 CH.sub.3                                                                    O  Cl  O                                              --        --   4-CO.sub.2 CH.sub.2 CH.sub.3                                                           O  Cl  CH.sub.2                                       --        --   4-NO.sub.2                                                                             O  Cl  O                                              --        --   2-CH.sub.3 O                                                                           O  Cl  O                                              --        --   2-Br     O  OC.sub.2 H.sub.5                                                                  CH.sub.2                                       --        --   2-CH.sub.3                                                                             O  OC.sub.2 H.sub.5                                                                  CH.sub.2                                       --        --   2-CO.sub.2 CH(CH.sub.3).sub.2                                                          O  OC.sub.2 H.sub.5                                                                  O                                              --        --   4-F      O  OC.sub.2 H.sub.5                                                                  CH.sub.2                                       --        --   2-NO.sub.2                                                                             O  OC.sub.2 H.sub.5                                                                  CH.sub.2                                       Cl        H    --       S  Cl  O                                              NO.sub.2  H    --       S  Cl  O                                              CO.sub.2 CH.sub.3                                                                       H    --       S  Cl  O                                              SO.sub.2 N(CH.sub.3).sub. 2                                                             H    --       S  Cl  O                                              Cl        5-Cl --       S  Cl  O                                              Cl        H    --       S  OC.sub.2 H.sub.5                                                                  O                                              NO.sub.2  H    --       S  OC.sub.2 H.sub.5                                                                  O                                              CO.sub.2 C.sub.2 H.sub.5                                                                H    --       S  OC.sub.2 H.sub.5                                                                  O                                               ##STR199##                                                                             H    --       S  OC.sub.2 H.sub.5                                                                  O                                              OCH.sub.3 5-OCH.sub.3                                                                        --       S  OC.sub.2 H.sub.5                                                                  O                                              SCH.sub.3 H    --       S  OC.sub.2 H.sub.5                                                                  O                                              SO.sub.2 C.sub.2 H.sub.5                                                                H    --       S  OC.sub.2 H.sub.5                                                                  O                                              --        --   2-Cl     S  Cl  O                                              --        --   4-F      S  Cl  O                                              --        --   2-NO.sub.2                                                                             S  Cl  O                                              --        --   4-CO.sub.2 CH.sub.3                                                                    S  Cl  O                                              --        --   2-OCH.sub.3                                                                            S  Cl  O                                              --        --   2-CH.sub.3                                                                             S  Cl  O                                              --        --   2-Cl     S  OC.sub.2 H.sub.5                                                                  O                                              --        --   2-NO.sub.2                                                                             S  OC.sub.2 H.sub.5                                                                  O                                              --        --   4-CO.sub.2 C.sub.2 H.sub.5                                                             S  OC.sub.2 H.sub.5                                                                  O                                              --        --   4-SCH.sub.3                                                                            S  OC.sub.2 H.sub.5                                                                  O                                              --        --   2-OCH.sub.3                                                                            S  OC.sub.2 H.sub.5                                                                  O                                              --        --   4-CH.sub.3                                                                             S  OC.sub.2 H.sub.5                                                                  O                                              __________________________________________________________________________

                                      TABLE IV-B                                  __________________________________________________________________________     ##STR200##                                                                    ##STR201##                                                                   R.sub.2    R.sub.3                                                                             R.sub.4   W  X   m.p.                                        __________________________________________________________________________    H          H     --        O  Cl                                              CO.sub.2 CH.sub.3                                                                        H     --        O  Cl  215-220°                             CO.sub.2 CH.sub.3                                                                        5-Cl  --        O  Cl                                              SO.sub.2 N(CH.sub.3).sub.2                                                               H     --        O  OC.sub.2 H.sub.5                                Cl         H     --        O  OC.sub.2 H.sub.5                                NO.sub.2   H     --        O  OC.sub.2 H.sub.5                                SO.sub.2 CH.sub.3                                                                        H     --        O  OC.sub.2 H.sub.5                                CO.sub.2 CH.sub.2 CHCH.sub.2                                                             H     --        O  OC.sub.2 H.sub.5                                CON(CH.sub.3).sub.2                                                                      H     --        O  OC.sub.2 H.sub.5                                 ##STR202##                                                                              H     --        O  OC.sub.2 H.sub.5                                F          H     --        O  OC.sub.2 H.sub.5                                --         --    2-CO.sub.2 CH.sub.3                                                                     O  Cl                                              --         --    4-CO.sub.2 CH.sub.2 CH.sub.3                                                            O  Cl                                              --         --    4-NO.sub.2                                                                              O  Cl                                              --         --    2-CH.sub.3 O                                                                            O  Cl                                              --         --    2-Br      O  OC.sub.2 H.sub.5                                --         --    2-CH.sub.3                                                                              O  OC.sub.2 H.sub.5                                --         --    2-CO.sub.2 CH(CH.sub.3).sub.2                                                           O  OC.sub.2 H.sub.5                                --         --    4-F       O  OC.sub.2 H.sub.5                                --         --    2-NO.sub.2                                                                              O  OC.sub.2 H.sub.5                                Cl         H     --        S  Cl                                              NO.sub.2   H     --        S  Cl                                              CO.sub.2 CH.sub.3                                                                        H     --        S  Cl                                              SO.sub.2 N(CH.sub.3).sub.2                                                               H     --        S  Cl                                              Cl         5-Cl  --        S  Cl                                              Cl         H     --        S  OC.sub.2 H.sub.5                                NO.sub.2   H     --        S  OC.sub.2 H.sub.5                                CO.sub.2 C.sub.2 H.sub.5                                                                 H     --        S  OC.sub.2 H.sub.5                                 ##STR203##                                                                              H     --        S  OC.sub.2 H.sub.5                                OCH.sub.3  5-OCH.sub.3                                                                         --        S  OC.sub.2 H.sub.5                                SCH.sub.3  H     --        S  OC.sub.2 H.sub.5                                SO.sub.2 C.sub.2 H.sub.5                                                                 H     --        S  OC.sub.2 H.sub.5                                Cl         H     --        S  Cl                                              NO.sub.2   H     --        S  Cl                                              CO.sub.2 CH.sub.3                                                                        H     --        S  Cl                                              Cl         5-Cl  --        S  Cl                                              SO.sub.2 N(C.sub.2 H.sub.5).sub.2                                                        H     --        S  Cl                                              Cl         H     --        S  OC.sub.2 H.sub.5                                NO.sub.2   H     --        S  OC.sub.2 H.sub.5                                CO.sub.2 CH.sub.3                                                                        H     --        S  OC.sub.2 H.sub.5                                SCH.sub.3  5-SCH.sub.3                                                                         --        S  OC.sub.2 H.sub.5                                CON(CH.sub.3).sub.2                                                                      H     --        S  OC.sub.2 H.sub.5                                SO.sub.2 N(CH.sub.3).sub.2                                                               H     --        S  OC.sub.2 H.sub.5                                --         --    2-Cl      S  Cl                                              --         --    4-F       S  Cl                                              --         --    2-NO.sub.2                                                                              S  Cl                                              --         --    4-CO.sub.2 CH.sub.3                                                                     S  Cl                                              --         --    2-OCH.sub.3                                                                             S  Cl                                              --         --    2-CH.sub.3                                                                              S  Cl                                              --         --    4-Cl      S  Cl                                              --         --    4-NO.sub.2                                                                              S  Cl                                              --         --    4-CO.sub.2 CH.sub.3                                                                     S  Cl                                              --         --    4-CO.sub.2 CH(CH.sub.3).sub.2                                                           S  Cl                                              --         --    2-Cl      S  OC.sub.2 H.sub.5                                --         --    2-NO.sub.2                                                                              S  OC.sub.2 H.sub.5                                --         --    4-CO.sub.2 C.sub.2 H.sub.5                                                              S  OC.sub.2 H.sub.5                                --         --    4-SCH.sub.3                                                                             S  OC.sub.2 H.sub.5                                --         --    2-OCH.sub.3                                                                             S  OC.sub.2 H.sub.5                                --         --    4-CH.sub.3                                                                              S  OC.sub.2 H.sub.5                                --         --    4-F       S  OC.sub.2 H.sub.5                                --         --    2-Br      2  OC.sub.2 H.sub.5                                --         --    2-NO.sub.2                                                                              S  OC.sub.2 H.sub.5                                --         --    4-CO.sub.2 CH.sub.3                                                                     S  OC.sub.2 H.sub.5                                --         --    2-C.sub.2 H.sub.5                                                                       S  OC.sub.2 H.sub.5                                H          H     --        O  H                                               CO.sub.2 CH.sub.3                                                                        H     --        O  H                                               CO.sub.2 CH.sub.3                                                                        5-Cl  --        O  H                                               SO.sub.2 N(CH.sub.3).sub.2                                                               H     --        O  H                                               Cl         H     --        O  H                                               NO.sub.2   H     --        O  H                                               SO.sub.2 CH.sub.3                                                                        H     --        O  H                                               CO.sub.2 CH.sub.2 CHCH.sub.2                                                             H     --        O  H                                               CON(CH.sub.3).sub.2                                                                      H     --        O  H                                                ##STR204##                                                                              H     --        O  H                                               F          H     --        O  H                                               --         --    2-CO.sub.2 CH.sub.3                                                                     O  H                                               --         --    4-CO.sub.2 CH.sub.2 CH.sub.3                                                            O  H                                               --         --    4-NO.sub.2                                                                              O  H                                               --         --    2-CH.sub.3 O                                                                            O  H                                               --         --    2-Br      O  H                                               --         --    2-CH.sub.3                                                                              O  H                                               --         --    2-CO.sub.2 CH(CH.sub.3).sub.2                                                           O  H                                               --         --    4-F       O  H                                               --         --    2-NO.sub.2                                                                              O  H                                               H          H     --        S  H                                               CO.sub.2 CH.sub.3                                                                        H     --        S  H                                               CO.sub.2 CH.sub.3                                                                        5-Cl  --        S  H                                               SO.sub.2 N(CH.sub.3).sub.2                                                               H     --        S  H                                               Cl         H     --        S  H                                               NO.sub.2   H     --        S  H                                               SO.sub.2 CH.sub.3                                                                        H     --        S  H                                               CO.sub.2 CH.sub.2 CHCH.sub.2                                                             H     --        S  H                                               CON(CH.sub.3).sub.2                                                                      H     --        S  H                                                ##STR205##                                                                              H     --        S  H                                               F          H     --        S  H                                               --         --    2-CO.sub.2 CH.sub.3                                                                     S  H                                               --         --    4-CO.sub.2 CH.sub.2 CH.sub.3                                                            S  H                                               --         --    4-NO.sub.2                                                                              S  H                                               --         --    2-CH.sub.3 O                                                                            S  H                                               --         --    2-Br      S  H                                               --         --    2-CH.sub.3                                                                              S  H                                               --         --    2-CO.sub.2 CH(CH.sub.3).sub.2                                                           S  H                                               --         --    4-F       S  H                                               --         --    2-NO.sub.2                                                                              S  H                                               __________________________________________________________________________

Compounds of Formula II are prepared according to the procedures ofEquations 2 and 5 and Example 9 wherein temperatures are given indegrees centrigrade.

EXAMPLE 9 MethylN'-(2-chlorophenylsulfonyl)-N-(5,6-dihydro-4-methylfuro[2,3-d]pyrimidin-2-yl)carbamimidothioate

To a suspension of 3.85 g2-chloro-N-[(5,6-dihydro-2-methylfuro[2,3-d]pyrimidine-2-yl)aminothioxomethyl]benzenesulfonamidein 150 ml of anhydrous tetrahydrofuran was added 4.3 ml of 3 M NaOCH₃/CH₃ OH solution. The reaction reaction mixture was refluxed for 1.25hour, whereupon 1.85 g of methyl iodide in 10 ml of anhydroustetrahydrofuran was added. After refluxing and stirring for anadditional 12 hours, the reaction mixture was cooled, solvent wasremoved under vacuum and the residue was recrystallized fromacetonitrile to yield 1 g of the product.

                                      TABLE V-a                                   __________________________________________________________________________     ##STR206##                                                                   R.sub.12   R.sub.2  R.sub.3                                                                            X     Y m.p.                                         __________________________________________________________________________    CH.sub.3   Cl       5-Cl CH.sub.3 O                                                                          O                                              CH.sub.3 CH.sub.2                                                                        Cl       5-Cl CH.sub.3                                                                            O                                              CH.sub.3   Cl       5-Cl CH.sub.3 CH.sub.2 O                                                                 O                                              CH.sub.3   CH.sub.3 5-CH.sub.3                                                                         H     O                                              CH.sub.3   CH.sub.3 5-CH.sub.3                                                                         CH.sub.3                                                                            O                                              CH.sub.3   CH.sub.3 H    CH.sub.3 O                                                                          O                                              CH.sub.3   CH.sub.3 H    CH.sub.3                                                                            O                                              CH.sub.3 (CH.sub.2).sub.3                                                                H        H    CH.sub.3 O                                                                          O                                              CH.sub.3   H        H    CH.sub.3                                                                            O                                              CH.sub.3 CH.sub.2                                                                        Cl       H    H     O                                              CH.sub.3   F        H    CH.sub.3                                                                            O                                              CH.sub.3   CH.sub.3 O                                                                             5-Cl CH.sub.3                                                                            O                                              CH.sub.3   Cl       6-Cl CH.sub.3                                                                            O                                              CH.sub.3   Cl       5-CH.sub.3                                                                         H     O                                              CH.sub.3   F        H    CH.sub.3 O                                                                          O                                              CH.sub.3   CH.sub.3 O                                                                             5-Cl CH.sub.3 O                                                                          O                                              CH.sub.3   NO.sub.2 H    CH.sub.3                                                                            O                                              CH.sub.3   NO.sub.2 H    CH.sub.3 O                                                                          O                                              CH.sub.3   SO.sub.2 N(CH.sub.3).sub.2                                                             H    CH.sub.3                                                                            O                                              CH.sub.3   CH.sub.3 SO                                                                            H    CH.sub.3                                                                            O                                              CH.sub.3   Cl       3-Cl H     O                                              (CH.sub.3).sub.2 CHCH.sub.2                                                              CH.sub.3 O                                                                             5-CH.sub.3 O                                                                       CH.sub.3                                                                            O                                              CH.sub.3   CF.sub.3 H    CH.sub.3                                                                            O                                              CH.sub.3   CH.sub.3 O                                                                             H    Cl    O                                              CH.sub.3   H        3-Cl CH.sub.3                                                                            O                                              CH.sub.3   H        3-F  CH.sub.3                                                                            O                                              CH.sub.3   Cl       H    CH.sub.3                                                                            O 161-162°                              CH.sub.3   H        3-CH.sub.3                                                                         CH.sub.3                                                                            O                                              (CH.sub.3).sub.2 CH                                                                      H        3-Br CH.sub.3 O                                                                          O                                              CH.sub.3   SO.sub.2 N(OCH.sub.3)CH.sub.3                                                          H    CH.sub.3                                                                            O                                              CH.sub.3   F        6-F  H     O                                              CH.sub.3   F        5-F  CH.sub.3                                                                            O                                              CH.sub.3   SO.sub.2 OCH.sub.2 CF.sub.3                                                            H    CH.sub.3                                                                            O                                              CH.sub.3   SO.sub.2 OCH.sub.2 CCl.sub.3                                                           H    H     O                                              CH.sub.3   Cl       5-CH.sub.3                                                                         CH.sub.3                                                                            O                                              CH.sub.3 (CH.sub.2).sub.3                                                                Cl       H    Cl    O                                              CH.sub.3 CH.sub.2                                                                        CH.sub.3 O                                                                             5-CH.sub.3 O                                                                       CH.sub.3 O                                                                          O                                               ##STR207##                                                                              CH.sub.3 O                                                                             5-CH.sub.3 O                                                                       H     O                                              CH.sub.3 (CH.sub.2).sub.3                                                                CH.sub.3 H    CH.sub.3 O                                                                          O                                              (CH.sub.3).sub.2 CH                                                                      CH.sub.3 H    CH.sub.3                                                                            O                                              CH.sub.3 (CH.sub.2).sub.4                                                                H        H    CH.sub.3                                                                            O                                              CH.sub.3   Cl       H    CH.sub.3 O                                                                          O                                              n-C.sub.7 H.sub.15                                                                       Cl       H    CH.sub.3                                                                            O 110-111.5°                            n-C.sub.10 H.sub.21                                                                      Cl       H    Cl    O                                               ##STR208##                                                                              Cl       H    CH.sub.3                                                                            O                                              CH.sub.3                                                                                  ##STR209##                                                                            H    CH.sub.3                                                                            O                                              CH.sub.2 CN                                                                               ##STR210##                                                                            H    CH.sub.3 O                                                                          O                                               ##STR211##                                                                              Cl       H    CH.sub.3                                                                            O 241-243°                               ##STR212##                                                                              F        H    CH.sub.3                                                                            O                                              CH.sub.2 CN                                                                              Cl       H    CH.sub.3                                                                            O                                              CH.sub.2 COOH                                                                            Cl       H    CH.sub.3                                                                            O                                               ##STR213##                                                                              Cl       H    CH.sub.3                                                                            O 115-188°(d)                           CH.sub.2C.sub.6 H.sub.5                                                                  Cl       H    CH.sub.3                                                                            O 140-142°                               ##STR214##                                                                              Cl       H    CH.sub.3                                                                            O                                               ##STR215##                                                                              Cl       H    H     O                                               ##STR216##                                                                              Cl       H    CH.sub.3                                                                            O                                              CH.sub.2 CN                                                                              CO.sub.2 CH.sub.3                                                                      H    CH.sub.3                                                                            O                                              CH.sub.2 CHCH.sub.2                                                                      CO.sub.2 CH.sub.3                                                                      H    CH.sub.3                                                                            O                                              CH.sub.2 CHCH.sub.2                                                                      Cl       H    Cl    O                                              CH.sub.2 CHCHCH.sub.3                                                                    Cl       H    CH.sub.3 O                                                                          O                                              CH.sub.2 CCH                                                                             CO.sub.2 CH(CH.sub.3).sub.2                                                            H    H     O                                              CH.sub.2 CONH.sub.2                                                                      Cl       H    CH.sub.3                                                                            O 150-152°                              (CH.sub.2).sub.5 CH.sub.3                                                                Cl       H    CH.sub.3 O                                                                          O                                              (CH.sub.2).sub.7 CH.sub.3                                                                Cl       H    CH.sub.3 O                                                                          O                                              n-C.sub.12 H.sub.25                                                                      Cl       H    CH.sub.3                                                                            O 83-85°                                 ##STR217##                                                                              CH.sub.3 O                                                                             5-CH.sub.3 O                                                                       CH.sub.3 O                                                                          O                                              CH.sub.3   CH.sub.3 O                                                                             5-CH.sub.3 O                                                                       CH.sub.3 O                                                                          O                                              CH.sub.2 CN                                                                              F        H    H     O                                               ##STR218##                                                                              NO.sub.2 H    CH.sub.3                                                                            O                                               ##STR219##                                                                              Br       5-Br CH.sub.3                                                                            O                                               ##STR220##                                                                              CON(CH.sub.3).sub.2                                                                    H    CH.sub.3 O                                                                          O                                               ##STR221##                                                                              CH.sub.3 (CH.sub.2).sub.5 SO.sub.2                                                     H    CH.sub.3 CH.sub.2 O                                                                 O                                               ##STR222##                                                                               ##STR223##                                                                            5-CH.sub.3                                                                         Cl    O                                               ##STR224##                                                                              CH.sub.3 5-CH.sub.3                                                                         CH.sub.3                                                                            O                                               ##STR225##                                                                              (CH.sub.3).sub.2 CH.sub.2 SO.sub.2                                                     H    H     O                                              CH.sub.3   SO.sub.2 N(C.sub.2 H.sub.5).sub.2                                                      H    CH.sub.3                                                                            O                                              C.sub.2 H.sub.5                                                                           ##STR226##                                                                            H    CH.sub.3                                                                            O                                              CH.sub.3   SO.sub.2 OCH.sub.2 CF.sub.3                                                            H    CH.sub.3                                                                            O                                              CH(CH.sub.3).sub.2                                                                       SO.sub.2 OCH.sub.2 CCl.sub.3                                                           H    CH.sub.3 O                                                                          O                                              __________________________________________________________________________

                                      TABLE V-b                                   __________________________________________________________________________     ##STR227##                                                                   R.sub.12     R.sub.3                                                                             R.sub.5     X    Y                                         __________________________________________________________________________    CH.sub.3     H     CH.sub.3    CH.sub.3                                                                           O                                         CH.sub.3     H     CH.sub.3    CH.sub.3 O                                                                         O                                         CH.sub.3 CH.sub.2                                                                          5-Cl  CH.sub.3    CH.sub.3 O                                                                         O                                         (CH.sub.3).sub.2 CH                                                                        5-Br  CH.sub.3    CH.sub.3                                                                           O                                         CH.sub.3 CH.sub.2                                                                          5-Cl  CH.sub.3    CH.sub.3                                                                           O                                         CH.sub.3 (CH.sub.2).sub.3                                                                  5-CH.sub.3 O                                                                        CH.sub.3    CH.sub.3                                                                           O                                         (CH.sub.3).sub.2 CHCH.sub.2                                                                5-CH.sub.3 O                                                                        CH.sub.3    CH.sub.3                                                                           O                                         CH.sub.3     5-CH.sub.3 O                                                                        CH.sub.3    CH.sub.3                                                                           O                                         CH.sub.3     H                                                                                    ##STR228## H    O                                         CH.sub.3 CH.sub.2 (CH.sub.3)CH                                                             H     CH.sub.3 (CH.sub.2).sub.3                                                                 CH.sub.3                                                                           O                                         CH.sub.3     5-CH.sub.3 O                                                                        CH.sub.3    CH.sub.3 O                                                                         O                                         CH.sub.3     3-CH.sub.3                                                                          CH.sub.3 CH.sub.2                                                                         CH.sub.3                                                                           O                                         C.sub.2 H.sub.5                                                                            H     CH.sub.3    CH.sub.3 O                                                                         O                                          ##STR229##  H     CH.sub.3    CH.sub.3 O                                                                         O                                         CH.sub.3     H     CH.sub.2 CHCH.sub.2                                                                       CH.sub.3 O                                                                         O                                         CH.sub.3     H     CH(CH.sub.3)CHCH.sub.2                                                                    CH.sub.3                                                                           O                                         CH.sub.2 CHCH.sub.2                                                                        H     CH.sub.3 OCH.sub.2 CH.sub.2                                                               CH.sub.3                                                                           O                                          ##STR230##  H                                                                                    ##STR231## H    O                                         CH.sub.2 CCH 5-Cl  CH.sub.3 CH.sub.2 OCH.sub.2 CH.sub.2                                                      CH.sub.3 O                                                                         O                                         n-C.sub.11 H.sub.23                                                                        5-F                                                                                  ##STR232## H    O                                         CH.sub.2 COOC.sub.2 H.sub.5                                                                6-Cl  CH.sub.3 CHCHCH.sub.2                                                                     CH.sub.3 O                                                                         O                                         CH.sub.3 OCH.sub.2 CH.sub.2                                                                5-Br  (CH.sub.3).sub.2 CH                                                                       CH.sub.3 O                                                                         O                                          ##STR233##  H     CH.sub.3    CH.sub.3                                                                           O                                          ##STR234##  H     CH.sub.3 OCH.sub.2 CH.sub. 2                                                              H    O                                         CH.sub.2 COOCH.sub.3                                                                       H     n-C.sub.6 H.sub.13                                                                        CH.sub.3                                                                           O                                         CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                       H     CH.sub.2CHCH.sub.2                                                                        H    O                                         CH(CH.sub.3).sub.2                                                                         H                                                                                    ##STR235## Cl   O                                         CH.sub.2 CCH 5-Cl                                                                                 ##STR236## Cl   O                                          ##STR237##  H     CH.sub.3    CH.sub.3 O                                                                         O                                          ##STR238##  3-F   CH.sub.3 CH.sub.2                                                                         CH.sub.3                                                                           O                                         CH.sub.2 CCH 6-CH.sub.3                                                                          CH.sub.3 (CH.sub.2).sub.2                                                                 H    O                                         CH.sub.2 CH.sub.2 CH.sub.3                                                                 6-Cl  CH.sub.2 CCl.sub.3                                                                        Cl   O                                          ##STR239##  H     (CH.sub.2).sub.3 CH.sub.3                                                                 Cl   O                                         (CH.sub.2).sub.5 CH.sub.3                                                                  H     CH.sub.2 CHCH.sub.2                                                                       H    O                                         CH.sub.2 COOH                                                                              5-Br  C.sub.2 H.sub.5                                                                           H    O                                         __________________________________________________________________________

                                      TABLE V-c                                   __________________________________________________________________________     ##STR240##                                                                   R.sub.12    R.sub.3                                                                            R.sub.8 R.sub.9 X     Y                                      __________________________________________________________________________    CH.sub.3 (CH.sub.2).sub.5                                                                 H    CH.sub.3                                                                              CH.sub.3                                                                              CH.sub.3 O                                                                          O                                      CH.sub.3    5-Cl CH.sub.3 CH.sub.2                                                                     CH.sub.3 CH.sub.2                                                                     CH.sub.3 O                                                                          O                                      CH.sub.3 (CH.sub.2).sub.3                                                                 6-Cl CH.sub.3                                                                              H       CH.sub.3 O                                                                          O                                      CH.sub.3 CH.sub.2                                                                         H    CH.sub.3                                                                              CH.sub.3                                                                              CH.sub.3 O                                                                          O                                      CH.sub.3    3-CH.sub.3                                                                         CH.sub.3 O                                                                            CH.sub.3                                                                              CH.sub.3 O                                                                          O                                      CH.sub.3    H    CH.sub.3 (CH.sub.2).sub.2                                                             CH.sub.3 (CH.sub.2).sub.2                                                             H     O                                      CH.sub.3    H    H       (CH.sub.3).sub.2 CH                                                                   CH.sub.3 O                                                                          O                                       ##STR241## H    CH.sub.3                                                                              CH.sub.3                                                                              CH.sub.3 O                                                                          O                                       ##STR242## 5-CH.sub.3                                                                         CH.sub.3 O                                                                            CH.sub.3                                                                              H     O                                       ##STR243## H    CH.sub.2CHCH.sub.2                                                                    CH.sub.2CHCH.sub.2                                                                    CH.sub.3 O                                                                          O                                      CH.sub.3    H    CH.sub.3                                                                              CH.sub.3                                                                              H     O                                      C.sub.2 H.sub.5                                                                           H    CH.sub.3                                                                              CH.sub.3                                                                              Cl    O                                       ##STR244## H    CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2                                                           CH.sub.3 CH.sub.2 O                                                                 O                                       ##STR245## 5-CH.sub.3 O                                                                       CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2                                                  H     O                                      -n-C.sub.12 H.sub.25                                                                      H    CH.sub.3 O                                                                            CH.sub.3                                                                              CH.sub.3                                                                            O                                      n-C.sub.10 H.sub.21                                                                       6-Cl H       H       CH.sub.3                                                                            O                                      CH.sub.3 OCH.sub.2 CH.sub.2                                                               5-F  H       CH.sub.3                                                                              CH.sub.3 O                                                                          O                                      CH.sub.2 CO.sub.2 CH.sub.3                                                                5-CH.sub.3                                                                         CH.sub.3 CH.sub.2                                                                     CH.sub.3                                                                              H     O                                       ##STR246## H    n-C.sub.4 H.sub.9                                                                     n-C.sub.4 H.sub.9                                                                     H     O                                       ##STR247## H    CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2                                                  CH.sub.3                                                                            O                                       ##STR248## H    CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2                                                          CH.sub.3 CH.sub.2 O                                                                 O                                       ##STR249## 6-Cl CH.sub.3 O                                                                            CH.sub.3                                                                              CH.sub.3 O                                                                          O                                      CH.sub.2 CHCH.sub.2                                                                       5-CH.sub.3 O                                                                       H       H       CH.sub.3 O                                                                          O                                      CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                      H    C.sub.2 H.sub.5                                                                       CH.sub.3                                                                              Cl    O                                      CH.sub.2 CN H     CH(CH.sub.3).sub.2                                                                   CH.sub.3                                                                              Cl    O                                      __________________________________________________________________________

                  TABLE V-d                                                       ______________________________________                                         ##STR250##                                                                   R.sub.12    R.sub.2       R.sub.3  X     Y                                    ______________________________________                                        CH.sub.3    SO.sub.2 N(CH.sub.3).sub.2                                                                  H        CH.sub.3                                                                            O                                    CH(CH.sub.3).sub.2                                                                        CO.sub.2 CH.sub.3                                                                           H        CH.sub.3 O                                                                          O                                     ##STR251## SO.sub.2 N(C.sub.2 H.sub.5).sub.2                                                           H        CH.sub.3                                                                            O                                    (CH.sub.2).sub.4 CH(CH.sub.3).sub.2                                                       CON(CH.sub.3).sub.2                                                                         H        H     O                                    (CH.sub.2).sub.7 CH.sub.3                                                                  ##STR252##   H        CH.sub.3                                                                            O                                    (CH.sub.2).sub.9 CH.sub.3                                                                 SO.sub.2 N(CH.sub.3).sub.2                                                                  H        CH.sub.3                                                                            O                                    (CH.sub.2).sub.11 CH.sub.3                                                                CON(OCH.sub.3 )CH.sub.3                                                                     5-Cl     C.sub.2 H.sub.5 O                                                                   O                                    CH.sub.2 COOH                                                                             SO.sub.2 N(CH.sub.3).sub.2                                                                  H        CH.sub.3                                                                            O                                     ##STR253## SO.sub.2 N(OCH.sub.3)CH.sub.3                                                               H        CH.sub.3 O                                                                          O                                    CH.sub.2 COOCH.sub.3                                                                       ##STR254##   H H      Cl    O                                     ##STR255##                                                                                ##STR256##   5-CH.sub.3                                                                             CH.sub.3 O                                                                          O                                     ##STR257## CO.sub.2 CH(CH.sub.3).sub.2                                                                 H        CH.sub.3                                                                            O                                     ##STR258## CON(C.sub.2 H.sub.5).sub.2                                                                  H        CH.sub.3 O                                                                          O                                     ##STR259## SO.sub.2 N(CH.sub.3).sub.2                                                                  6-OCH.sub.3                                                                            C.sub.2 H.sub.5 O                                                                   O                                    CH.sub.2 CHCH.sub.2                                                                        ##STR260##   H        CH.sub.3 O                                                                          O                                    CH.sub.2 CCH                                                                              CO.sub.2 CH.sub. 3                                                                          H        Cl    O                                    CH.sub.2 CH.sub.2 OCH.sub.3                                                                ##STR261##   H        CH.sub.3 O                                                                          O                                    CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                      CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                         5-F      CH.sub.3                                                                            O                                    CH.sub.2 CN SO.sub.2 N(OCH.sub.3)CH.sub.3                                                               H        H     O                                    ______________________________________                                    

                  TABLE V-e                                                       ______________________________________                                         ##STR262##                                                                   R.sub.12       R.sub.4     X         Y                                        ______________________________________                                        CH.sub.3       H           CH.sub.3 O                                                                              O                                        CH.sub.3       2-Cl        CH.sub.3  O                                        CH.sub.3 (CH.sub.2).sub.3                                                                    4-F         CH.sub.3  O                                        CH.sub.3 CH.sub.2 (CH.sub.3)CH                                                               2-SCH.sub.3 CH.sub.3 O                                                                              O                                         ##STR263##    2-Br        CH.sub.3 O                                                                              O                                         ##STR264##    2-OC.sub.2 H.sub.5                                                                        CH.sub.3 O                                                                              O                                        CH.sub.3 OCH.sub.2 CH.sub.2 CH.sub.2                                                         4-NO.sub.2  CH.sub.3 O                                                                              O                                        CH.sub.2 COOH  2-F         CH.sub.3 O                                                                              O                                        CH.sub.2 COOCH.sub.3                                                                         2-CH(CH.sub.3).sub.2                                                                      CH.sub.3 CH.sub.2 O                                                                     O                                         ##STR265##    4-OCH.sub.3 CH.sub.3 O                                                                              O                                        CH.sub.3 CH.sub. 2                                                                           2-SO.sub.2 CH.sub.3                                                                       Cl        O                                         ##STR266##    2-F         H         O                                         ##STR267##    4-SCH.sub.3 Cl        O                                        CH.sub.3 O(CH.sub.2).sub.3                                                                   2-Br        H         O                                         ##STR268##    2-CO.sub.2 C.sub.2 H.sub.5                                                                H         O                                        CH.sub.2CHCH.sub.2 CH.sub.2                                                                  2-NO.sub.2  Cl        O                                         ##STR269##    4-Cl        Cl        O                                        ______________________________________                                    

                  TABLE V-f                                                       ______________________________________                                         ##STR270##                                                                   R.sub.12      R.sub.4    X        Y    m.p.                                   ______________________________________                                        CH.sub.3      2-Cl       CH.sub.3 O                                                                             O                                           CH.sub.3 CH.sub.2                                                                           4-Cl       H        O                                           CH.sub.3 (CH.sub.2).sub.2                                                                   2-F        CH.sub.3 O                                           CH.sub.3      4-Br       C.sub.2 H.sub.5 O                                                                      O                                           (CH.sub.3).sub.2 CHCH.sub.2                                                                 4-NO.sub.2 CH.sub.3 O                                                                             O                                           CH.sub.2 CHCH.sub.2                                                                         2-C.sub.2 H.sub.5                                                                        Cl       O                                            ##STR271##   2-OCH.sub.3                                                                              CH.sub.3 O                                            ##STR272##   4-CO.sub.2 C.sub.2 H.sub.5                                                               CH.sub.3 O                                           CH.sub.2 COOH 2-SC.sub.2 H.sub.5                                                                       H        O                                            ##STR273##   2-Cl       CH.sub. 3                                                                              O                                           CH.sub.3 OCH.sub.2 CH.sub.2                                                                 2-Br       C.sub.2 H.sub.5 O                                                                      O                                           ______________________________________                                    

The compounds of Table VI are useful as intermediates for thepreparation of many of the ureas of Tables I through V. By applicationof one or more of the procedures of Examples 10 through 13 and/or themethods described above, and using the appropriate reactants, thecompounds of Table VI can be prepared.

Conversion of these compounds to ureas can be accomplished by theprocedure of Example 14 and/or the methods described above.

EXAMPLE 10 Methyl2-[[(6,7-dihydro-4-methoxy-5H-cyclopentapyrimidin-2-yl)aminothioxomethyl]aminosulfonyl]benzoate

A mixture of 4.3 g of methyl 2-(aminosulfonyl)-benzoate, 4.2 g of6,7-dihydro-2-isothiocyanato-4-methoxy-5H-cyclopentapyrimidine and 2.2 gof anhydrous potassium carbonate in 70 ml of acetone was warmed to 40°with stirring. After 2 hours, a thick precipitate formed and stirringwas continued for three more hours at ambient temperature. Theprecipitate was filtered, suspended in 150 ml of water, stirred and thepH adjusted to 2 by the addition of hydrochloric acid. The white solidwas filtered, washed with cold water and dried to yield 4.2 g ofproduct.

EXAMPLE 112-Chloro-N[(5,6-dihydro-4-methylfuro[2,3-d]pyrimidin-2-yl)aminothioxomethyl]benzenesulfonamide

To a dry stirred mixture of 4.9 g of5,6-dihydro-4-methylfuro[2,3-d]pyrimidin-2-amine in 125 ml ofacetonitrile at ambient temperature was added 7.6 g of 2-chlorophenylsulfonylisothiocyanate. The resulting mixture was stirred at refluxtemperature (84°) for 24 hours. After cooling the reaction mixture, awhite solid was filtered and washed with acetonitrile to yield 10.8 g ofproduct, m.p. 190-191 dec. Elemental analyses, infrared spectrum andnuclear magnetic resonance spectrum indicated the title compound.

EXAMPLE 12 MethylN-(6,7-dihydro-4-methyl-5H-cyclopentapyrimidin-2-yl)N'-(2,5-dimethoxyphenylsulfonyl)carbamimidothioate

1.5 grams of 6,7-dihydro-4-methyl-5H-cyclopentapyrimidin-2-amine wasdissolved in a mixture of 20 ml of anhydrous tetrahydrofuran and 60 mlof anhydrous dimethylformamide. 0.48 grams of sodium hydride (50%mineral oil dispersion) was added. The reaction was stirred untilhydrogen evolution ceased. 2.75 grams ofN(2,5-dimethoxyphenylsulfonyl)carbonimidodithoic acid, 5,5-dimethylester was added all at once. The reaction mixture was stirred 24 hoursat ambient temperature. The mixture was poured into 300 ml of water andacidified to pH 5 with 20% hydrochloric acid. The mixture was filtered.The solid obtained was recrystallized from ethyl acetate to yield 1 g ofproduct.

EXAMPLE 13 Methyl2-[[1-(6,7-dihydro-4-methoxy-5H-cyclopentapyrimidin-2-yl-amino)-1-(ethylthio)methylene]aminosulfonyl]benzoate

To a suspension at 4.2 g of methyl2-[[(6,7-dihydro-4-methoxy-5H-cyclopentapyrimin-2-yl)aminothioxomethyl]aminosulfonyl]benzoatein 200 ml of anhydrous tetrahydrofuran was added 4.3 ml of 3 M NaOCH₃/CH₃ OH solution. The reaction was refluxed for 5 min. whereupon 2 g ofethyl iodide in 10 ml of anhydrous tetrahydrofuran was added. Afterrefluxing and stirring for an additional 6 hours, the reaction mixturewas cooled, solvent was removed under vacuum and the residue wasrecrystallized from acetonitrile to yield 0.5 g of the product.

EXAMPLE 14 Methyl2-[[(6,7-dihydro-4-methoxy-5H-cyclopentapyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzoate

A solution of 3.2 g of methyl2-[[1-(6,7-dihydro-4-methoxy-5H-cyclopentapyrimidin-2-ylamino)-1-(ethylthio)methylene]aminosulfonyl]benzoatein 75 ml of acetone is treated with 3.0 g of mercuric oxide and stirredat room temperature for 3 days. The mercury salts are removed byfiltration and the solvent is evaporated to yield the solid product.

                  TABLE VI-a                                                      ______________________________________                                         ##STR274##                                                                    ##STR275##                                                                   R.sub.2     R.sub.3                                                                              R.sub.4    q'  Xm.p.(°C.)                           ______________________________________                                        CO.sub.2 CH.sub.3                                                                         H      --         3   OCH.sub.3                                   Cl          H      --         3   OCH.sub.3  198-199°                  Cl          H      --         3   CH.sub.3 190-191°                    SCH.sub.3   H      --         3   CH.sub.3                                    SO.sub.2 CH.sub.3                                                                         H      --         4   CH.sub.3                                    NO.sub.2    5-Cl   --         4   OCH.sub.3                                   CH.sub.3    H      --         4   OC.sub.2 H.sub.5                            CON(CH.sub.3).sub.2                                                                       H      --         3   CH.sub.3                                     ##STR276## H      --         4   CH.sub.3                                    F           H      --         3   OCH.sub.3                                   CO.sub.2 C.sub.2 H.sub.5                                                                  H      --         4   CH.sub.3                                    CO.sub.2 CH.sub.2 CHCH.sub.2                                                              H      --         3   H                                           CO.sub.2 CH(CH.sub.3).sub.2                                                               H      --         4   H                                           SO.sub.2 N(CH.sub.3).sub.2                                                                H      --         4   CH.sub.3                                    SO.sub.2 N(OCH.sub.3)CH.sub.3                                                             5-Br   --         3   OCH.sub.3                                   Br          H      --         4   Cl                                          CON(C.sub.2 H.sub.5).sub.2                                                                H      --         3   Cl                                          CF.sub.3    H      --         3   H                                           SO.sub.2 OCH.sub.2 CF.sub.3                                                               H      --         4   CH.sub.3                                    --          --     H          3   CH.sub.3                                    --          --     2-Cl       4   CH.sub.3                                    --          --     2-Br       3   CH.sub.3                                    --          --     2-NO.sub.2 4   OCH.sub.3                                   --          --     2-CO.sub.2 CH.sub.3                                                                      3   OCH.sub.3                                   --          --     4-NO.sub.2 4   OCH.sub.3                                   --          --     4-OCH.sub.3                                                                              3   OCH.sub.3                                   --          --     2-CH(CH.sub.3).sub.2                                                                     4   CH.sub.3                                    --          --     2-F        4   CH.sub.3                                    --          --     4-OCH.sub.2 CH.sub.3                                                                     3   OCH.sub.3                                   --          --     4-Br       3   OCH.sub.2 CH.sub.3                          ______________________________________                                    

                                      TABLE VI-b                                  __________________________________________________________________________     ##STR277##                                                                    ##STR278##                                                                   R.sub.12   R.sub.2  R.sub.3                                                                           R.sub.4                                                                             q'                                                                              X   m.p.(°C.)                          __________________________________________________________________________    C.sub.2 H.sub.5                                                                          Cl       H   --    3 CH.sub.3                                                                          162-163°                           CH.sub.3   Br       H   --    4 CH.sub.3                                      CH.sub.3   NO.sub.2 5-Cl                                                                              --    4 OCH.sub.3                                     C.sub.12 H.sub.25                                                                        CH.sub.3 H   --    4 OCH.sub.3                                     CH.sub.3   CO.sub.2 CH.sub.3                                                                      H   --    3 H                                             CH.sub.3   CON(CH.sub.3).sub.2                                                                    H   --    3 H                                             CH.sub.3   CON(C.sub. 2 H.sub.5).sub.2                                                            H   --    3 CH.sub.3                                      C.sub.2 H.sub.5                                                                          CON(OCH.sub.3)CH.sub.3                                                                 H   --    4 CH.sub.3                                      C.sub.4 H.sub.9                                                                          CONHCH.sub.3                                                                           H   --    4 CH.sub.3                                      CH.sub.3   SO.sub.2 N(CH.sub.3).sub.2                                                             5-NO.sub.2                                                                        --    4 OCH.sub.3                                     CH.sub.2 CO.sub.2 CH.sub.3                                                               SO.sub.2 C.sub.2 H.sub.5                                                               H   --    4 OCH.sub.3                                     CH.sub.2 C.sub.6 H.sub.5                                                                 SO.sub.2 OCH.sub.2 CF.sub.3                                                            3-F --    3 OCH.sub.3                                     CH(CH.sub.3)CO.sub.2 CH.sub.3                                                            CF.sub.3 H   --    3 OC.sub.2 H.sub.5                              CH.sub.2 CHCH.sub.2                                                                      CO.sub.2 CH.sub.2 CH.sub.3                                                             H   --    3 OC.sub.2 H.sub.5                              CH.sub.2 CCH                                                                             Cl       6-NO.sub.2                                                                        --    3 Cl                                            CH.sub.2 CH.sub.2 OCH.sub.3                                                              CO.sub.2 CH(CH.sub.3).sub.2                                                            H   --    4 Cl                                            CH.sub.2 CO.sub.2 H                                                                      OCH.sub.3                                                                              H   --    4 H                                              ##STR279##                                                                              --       --  4-Cl  4 H                                             CH.sub.3   --       --  2-NO.sub. 2                                                                         4 CH.sub.3                                       ##STR280##                                                                              --       --  4-CO.sub.2 CH.sub.3                                                                 3 CH.sub.3                                      CH.sub.3   --       --  2-Br  3 CH.sub.3                                       ##STR281##                                                                              --       --  2-OCH.sub.3                                                                         3 OCH.sub.3                                     C.sub.3 H.sub.7                                                                          --       --  4-CH.sub.2 CH.sub.3                                                                 3 OCH.sub.3                                     CH(CH.sub.3)CO.sub.2 C.sub.2 H.sub.5                                                     --       --  2-Cl  4 OCH.sub.3                                     __________________________________________________________________________

Formulations

Useful formulations of the compounds of Formulas I and II can beprepared in conventional ways. They include dusts, granules, pellets,suspensions, emulsions, wettable powders, emulsifiable concentrates andthe like. Many of these can be applied directly. Sprayable formulationscan be extended in suitable media and used at spray volumes of from afew liters to several hundred liters per hectare. The formulations,broadly, contain about 0.1% to 99% by weight of active ingredient(s) andat least one of (a) about 0.1% to 20% surfactant(s) and (b) about 1% to99.9% solid or liquid diluents(s). More specifically, they will containthese ingredients in the approximate proportions set forth in Table VII.

                  TABLE VII                                                       ______________________________________                                                   Weight Percent*                                                               Active              Surfac-                                                   Ingredient                                                                              Diluent(s)                                                                              tant(s)                                        ______________________________________                                        Wettable Powders                                                                           20-90        0-74     1-10                                       Oil Suspensions,                                                              Solutions, Emulsions                                                          (including Emulsifi-                                                          able Concentrates)                                                                          3-50       40-95     0-15                                       Aqueous Suspensions                                                                        10-50       40-84     1-20                                       Dusts         1-25       70-99     0-5                                        Granules and Pellets                                                                       0.1-95        5-99.9  0-15                                       ______________________________________                                         *Active Ingredient plus at least one of a Surfactant or a Diluent equals      100 weight percent.                                                      

Lower or higher levels of active ingredient can, of course, be presentdepending on the intended use and the physical properties of thecompound. Higher ratios of surfactant to active ingredient are sometimesdesirable, and are achieved by incorporation into the formulation, or bytank mixing.

Some typical solid diluents are described in Watkins, et al., "Handbookof Insecticide Dust Diluents and Carriers", 2nd Ed., Dorland Books,Caldwell, New Jersey, but other solids, either mined or manufactured,may be used. The more absorptive diluents are preferred for wettablepowders and the denser ones for dusts. Typical liquid diluents andsolvents are described in Marsden, "Solvents Guide", 2nd Ed.,Interscience, New York, 1950. Solubility under 0.1% is preferred forsuspension concentrates, solution concentrates are preferably stableagainst phase separation at 0° C. "McCutcheon's Detergents andEmulsifiers Annual", MC Publishing Corp., Ridgewood, New Jersey, as wellas Sisely and Wood, "Encyclopedia of Surface Active Agents", ChemicalPublishing Co., Inc., New York, 1964, list surfactants and recommendeduses. All formulations can contain minor amounts of additives to reducefoaming, caking, corrosion, microbiological growth, etc.

The methods of making such compositions are well known. Solutions areprepared by simply mixing the ingredients. Fine solid compositions aremade by blending, and usually, grinding as in a hammer or fluid energymill. Suspensions are prepared by wet milling (see for example, Littler,U.S. Pat. No. 3,060,084). Granules and pellets may be made by sprayingthe active material on preformed granular carriers or by agglomerationtechniques. See J. E. Browning, "Agglomeration", Chemical Engineering,Dec. 4, 1967, pp. 147ff. and "Perry's Chemical Engineer's Handbook", 4thEd., McGraw-Hill, New York, 1963, pp. 8-59ff.

For further information regarding the art of formulation, see forexample:

H. M. Loux, U.S. Pat. No. 3,235,361, Col. 6, line 16 through Col. 7,line 19 and Examples 10 through 41.

R. W. Luckenbaugh, U.S. Pat. No. 3,309,192, Col. 5, line 43 through Col.7, line 62 and Examples 8, 12, 15, 39, 41, 52, 53, 58, 132, 138-140,162-164, 166, 167, 169-182.

H. Gysin and E. Knusli, U.S. Pat. No. 2,891,855, Col. 3, line 66 throughCol. 5, line 17 and Examples 1-4.

G. C. Klingman, "Weed Control as a Science", John Wiley & Sons, Inc.,New York, 1961, pp. 81-96.

J. D. Fryer and S. A. Evans, "Weed Control Handbook", 5th Ed., BlackwellScientific Publications, Oxford, 1968, pp. 101-103.

The disclosures of the above-cited references are herein incorporated byreference.

Unless indicated otherwise, all parts are by weight in the followingexamples.

EXAMPLE 15

    ______________________________________                                        Wettable Powder                                                               ______________________________________                                        N-[(6,7-dihydro-4-methyl-5H-cyclopentapyrimidin-2-yl)-                        aminocarbonyl]-2-nitrobenzenesulfonamide                                                                  40%                                               dioctyl sodium sulfosuccinate                                                                             1.5%                                              sodium ligninsulfonate       3%                                               low viscosity methyl cellulose                                                                            1.5%                                              attapulgite                 54%                                               ______________________________________                                    

The ingredients are thoroughly blended, passed through an air mill, toproduce an average particle size under 15 microns, reblended, and siftedthrough a U.S.S. No. 50 sieve (0.3 mm opening) before packaging.

EXAMPLE 16

    ______________________________________                                        Granule                                                                       ______________________________________                                        wettable powder of Example 15                                                                       10%                                                     attapulgite granules  90%                                                     (U.S.S. #20-40; 0.84-0.42 mm)                                                 ______________________________________                                    

A slurry of wettable powder containing 25% solids is sprayed on thesurface of attapulgite granules in a double-cone blended. The granulesare dried and packaged.

EXAMPLE 17

    ______________________________________                                        Wettable Powder                                                               ______________________________________                                        N-[(6,7-dihydro-4-methoxy-5H-cyclopentapyrimidin-2-yl)-                       aminocarbonyl]-2-nitrobenzenesulfonamide                                                                   80%                                              Sodium alkylnaphthalenesulfonate                                                                           2%                                               sodium ligninsulfonate       2%                                               synthetic amorphous silica   3%                                               kaolinite                    13%                                              ______________________________________                                    

The ingredients are blended and ground in a hammer mill to produce anaverage particle size under 100 microns. The material is reblended,sifted through a U.S.S. #50 sieve and packaged.

EXAMPLE 18

    ______________________________________                                        Granule                                                                       ______________________________________                                        wettable powder of Example 17                                                                       15%                                                     gypsum                69%                                                     potassium sulfate     16%                                                     ______________________________________                                    

The ingredients are blended in a rotating mixer and water sprayed on toaccomplish granulation. When most of the material has reached thedesired range of 1.0 to 0.42 mm. (U.S.S. #18 to 40 sieves), the granulesare removed, dried, and screened. Oversize material is crushed toproduce additional material in the desired range. These granules contain12% active ingredient.

EXAMPLE 19

    ______________________________________                                        Wettable Powder                                                               ______________________________________                                        N-[(6,7-dihydro-4-methyl-5H-cyclopentapyrimidin-2-yl)-                        aminocarbonyl]-2-(methoxycarbonyl)benzenesul-                                 fonamide                    65%                                               dodecylphenol polyethylene glycol                                             ether                       2%                                                sodium ligninsulfonate      4%                                                sodium silicoaluminate      6%                                                montmorillonite (calcined)  23%                                               ______________________________________                                    

The ingredients are thoroughly blended. The liquid surfactant is addedby spraying upon the solid ingredients in the blender. After grinding ina hammer mill to produce particles essentially all below 100 microns,the material is reblended, sifted through a U.S.S. No. 50 sieve (0.3 mmopening) and packaged.

EXAMPLE 20

    ______________________________________                                        High Strength Concentrate                                                     ______________________________________                                        N-[(6,7-dihydro-4-methoxy-5H-cyclopentapyrimidin-2-yl)-                       aminocarbonyl]-2-nitrobenzenesulfonamide                                                                   98.5%                                            silica aerogel               0.5%                                             synthetic amorphous fine silica                                                                            1.0%                                             ______________________________________                                    

The ingredients are blended and ground in a hammer mill to produce ahigh strength concentrate essentially all passing a U.S.S. No. 50 sieve(0.3 mm openings). This material may then be formulated in a variety ofways.

EXAMPLE 21

    ______________________________________                                        Aqueous Suspension                                                            ______________________________________                                        N-[(6,7-dihydro-4-methyl-5H-cyclopentapyrimidin-2-yl)                         aminocarbonyl]2-(methoxycarbonyl)benzenesul-                                  fonamide                    25%                                               hydrated attapulgite         3%                                               crude calcium ligninsulfonate                                                                             10%                                               sodium dihydrogen phosphate  0.5%                                             water                       61.5%                                             ______________________________________                                    

The ingredients are ground together in a ball or roller mill until thesolid particles have been reduced to diameters under 10 microns.

EXAMPLE 22

    ______________________________________                                        Oil Suspension                                                                ______________________________________                                        N-[(6,7-dihydro-4-methyl-5H-cyclopentapyrimidin-2-yl)-                        aminocarbonyl-2-nitrobenzenesulfonamide                                                                   25%                                               polyoxyethylene sorbitol hexaoleate                                                                        5%                                               highly aliphatic hydrocarbon oil                                                                          70%                                               ______________________________________                                    

The ingredients are ground together in a sand mill until the solidparticles have been reduced to under about 5 microns. The resultingsuspension may be applied directly, but preferably after being extendedwith oils or emulsified in water.

EXAMPLE 23

    ______________________________________                                        Extruded Pellet                                                               ______________________________________                                        N-[(6,7-dihydro-4-methyl-5H-cyclopentapyrimidin-2-yl)-                        aminocarbonyl]-2-(methoxycarbonyl)benzenesulfon-                              amide                       25%                                               anhydrous sodium sulfate    10%                                               crude calcium ligninsulfonate                                                                              5%                                               sodium alkylnaphthalenesulfonate                                                                           1%                                               calcium/magnesium bentonite 59%                                               ______________________________________                                    

The ingredients are blended, hammer milled and then moistened with about12% water. The mixture is extruded as cylinders about 3 mm diameterwhich are cut to produce pellets about 3 mm long. These may be useddirectly after drying, or the dried pellets may be crushed to pass aU.S.S. No. 20 sieve (0.84 mm openings). The granules held on a U.S.S.No. 40 sieve (0.42 mm openings) may be packaged for use and the finesrecycled.

Utility

The compounds of the present invention are powerful herbicides. Theyhave utility for broad-spectrum pre- and/or post-emergence weed controlin areas where complete control of all vegetation is desired, such asaround fuel storage tanks, ammunition depots, industrial storage areas,parking lots, drive-in theaters, around billboards, highway and railroadstructures. Alternatively, the subject compounds are useful for theselective pre- or post-emergence weed control in crops, such as wheatand soybeans.

The rates of application for the compounds of the invention aredetermined by a number of factors, including their use as selective orgeneral herbicides, the crop species involved, the types of weeds to becontrolled, weather and climate, formulations selected, mode ofapplication, amount of foliage present, etc. In general terms, thesubject compounds should be applied at levels of around 0.02 to 10kg/ha, the lower rates being suggested for use on lighter soils and/orthose having a low organic matter content, for selective weed control orfor situations where only short-term persistence is required.

The compounds of the invention may be used in combination with any othercommercial herbicide examples of which are those of the triazine,triazole, uracil, urea, amide, diphenylether, carbamate and bipyridyliumtypes.

The herbicidal properties of the subject compounds were discovered in anumber of greenhouse tests. The test procedures and results follow.

Test A

Seeds of crabgrass (Digitaria spp.), barnyardgrass (Echinochloacrusgalli), wild oats (Avena fatua), Cassia tora, morningglory (Ipomeoeaspp.), cocklebur (Xanthium spp.), Sorghum, corn, soybean, rice, wheat aswell as nutsedge tubers were planted in a growth medium and treatedpreemergence with the chemicals dissolved in a non-phytotoxic solvent.At the same time, cotton having five leaves (including cotyledonaryones), bush beans with the third trifoliolate leaf expanding, crabgrass,barnyardgrass and wild oats with two leaves, cassia with three leaves(including cotyledonary ones), morningglory and cocklebur with fourleaves (including the cotyledonary ones), sorghum and corn with fourleaves, soybean with two cotyledonary leaves, rice with three leaves,wheat with one leaf, and nutsedge with three-five leaves were sprayed.Treated plants and controls were maintained in a greenhouse for sixteendays, whereupon all species were compared to controls and visually ratedfor response to treatment. The ratings are based on a numerical scaleextending from 0=no injury, to 10=complete kill. The accompanyingdescriptive symbols have the following meanings: G=growth retardation;C=chlorosis/necrosis; D=defoliation; S=albinism; 6F=delayed flowering;6Y=abscised buds or flowers; U=unusual pigmentation; E=emergenceinhibition; X=axillary stimulation; and H=formative effects. The ratingsfor the compounds tested by this procedure are presented in Table A. Itwill be seen that certain of the compounds tested have utility forselective pre-emergence weed control in wheat and soybeans.

    TABLE A      Post-emergence          Barn-         Bush-  Morning- Cockle-  Nut-     Crab- yard Wild  kg/ha bean Cotton glory bur Cassia sedge grass grass     oats Wheat Corn Soybean Rice Sorghum      ##STR282##      0.4 9C 9G,6C 10C 9C 9C 10C 9C 10C 9G,5C 8G,2C 9H,5U 9C 9C 9H,2U      ##STR283##      0.4 9C 10C 10C 9C 9C 2C,8G 5C,8G 9C 9C 9C 9C 9C 6C,9G 9C      ##STR284##      2 9C 9C 10C 9C 9C 8C 9C 9C 9C 8C 9U,9G 9C 5C,8G 5U,9G    " 0.4 9C 6C,9G     8C 9C 9C 5C,9G 9C 6C,9G 3C,7G 3C,8G 9C 6C,9G 5C,9G 9G      ##STR285##      2 9D,9G 3C,5G 3C,9G 5C,9G 3C 4G 2C,6G 2C 1C 2C 1C,5H 6H 8G 8H    " 0.4     5C,7G,6Y 1C,2G 1C,8G 2C,7G 1H 2C 2C 2C 0 0 6H 8H 5G 6H      ##STR286##      0.4 6C,8G,6Y 3C,5G 10C 9C 1C,8G 5C,9G 3C,8G 3C,8H 2C 1C,6G 2C,9H 3H,9G     5C,9G 7H      ##STR287##      2 9C 8C,9G 10C 10C 5C,8G 9C 9C 10C 5C,8G 5U,8G 9C 9C 9C 9C    " 0.4 9C     9C,9G 10C 10C 5C,8G 10C 9C 10C 5C,9G 5U,8G 10C 9C 9C 9C      ##STR288##      2 1C 0 1C 0 0 0 0 0 0 0 0 0 0 0    " 0.4 0 0 2C 0 0 0 0 0 0 0 0 0 0 0      ##STR289##      2 5C,9G 2C,2H,4G 10C 2C,9G 5C,7G 0 3C,7G 9C 2C,6G 1C,6G 2C,9H 1C,9H     5C,9G 3H,9G    " 0.4 5C,9G 2C,2H 5C,9G 1C 5C,9G 0 2C,7G 3C,7H 3G 2G     1C,4H 6H 5C,9G 1C,6G      ##STR290##      2 9D,9G 5C,6G 5C,7G 1C 4H 2C,7G 1C,5G 2C,9H 2C,7G 9H 9H 5H,9G 4C,9G     2C,9G      ##STR291##      2 2C 1C 1C 0 1C 0 0 2H 0 0 6H 6H 5G 5G    " 0.4 1C,1H 0 0 0 0 0 0 0 0 0     0 0 0 0      ##STR292##      0.4 9C 2C,6G 5C,9G 2C 3C 2G 1C 2C,7G 1C 1C 1C,6G 3C,8G 7G 1C,6G      ##STR293##      0.4 9C 2C,6G 9C 1C,3H 2C,7G 2G 2C,7G 5C,9H 1C,8G 2C,7G 2C,9G 5C,9G     3C,8G 2C,9G      ##STR294##      0.4 3C,5G,6Y 1C 3G 1C -- 0 0 0 0 0 0 0 0 0      ##STR295##      0.4 8C 2C 5C,8G 2C 1C 2G 0 3C,5G 1C 0 1C,3G 1C 1C,3G 2C,7G      ##STR296##      1/10 9D,9G,6Y 5C,9G 9C 3C,9G 3C,9G 1C,7G 9C 10C 9C 1C,7G 9C 9C 9C 10C      ##STR297##      2 5C,9G,6Y 3C,9G 10C 1C,8G 2C,5G 1C,9G 1C,7G 9C 1C,7G 4C,8G 5C,9G 3C,9G     3C,9G 2C,9G    " 0.4 6C,9G,6Y 2C,2H,8G 2C,5G 2C 3C 7G 2G 3C,9H 3C,5G     2C,4G 2C,7H 2C,8G 5C,9G 9G      ##STR298##      2 2H,6F 1H 2H 1C 0 0 0 0 0 0 0 4H -- 0    " 0.4 0 0 1H 0 0 0 0 0 0 0 0     2H 0 0      ##STR299##      0.4 7C 9G 6C 9G 5C 9G 9C 5C 7G 1C 8G 9C 9C 9C 9C 3U 9G 10C 9C 9C      ##STR300##      2 6C 9G 6Y 9C 10C 10C 9C 1C 9G 9C 9C 1C 3G 2C 7G 2C 9G 6C 9G 7G 2C 9G      " 0.4 6C 8G 6Y 5C 9G 10C 9C 3C 6G 3G 2C 8G 9C 0 1C 5G 2C 7H 3C 8G 2C 7G     1C 7H      ##STR301##      0.4 9D 9G 6Y 9C 10C 3C 9G 5C 9G 1C 8G 3C 6G 5C 9H 2C 8H 3C 7G 8U 9G 3C     9G 6C 9G 3C 9G      ##STR302##      0.4 7C 9G 9C 10C 9C 9C 4C 9G 4C 9G 10C 5C 9G 4C 9G 9C 9C 5C 9G 10C      ##STR303##      0.4 3C 9G 6Y 4C 9G 10C 3C 9G 3C 5G 2G 2G 3C 9H 8G 6G 5X 2C 9H 3C 9G 5C     9G 5C 9G      ##STR304##      0.4 6C 9G 6Y 3C 3H 9G 10C 1C 4G 2C 6G 5G 5C 9G 5C 9H 1C 5G 1C 5G 4C 9G     2C 8G 5X 7C 2C 9G      ##STR305##      0.4 5C,9G 5C,9G 9C 5C,9G 3C 0 1C,5G 3C,9H 4G 0 8H 2C,9G 9C 9H      ##STR306##      0.4 3S,9G,6Y 2C,7G 2C,9G 1C,6G 2C,5G 0 2G 2C,5H 0 0 1C,8G 1C,6G 1C,3G     1C,7H      ##STR307##      0.4 3S,9G,6Y 2C,2H,8G 3C,9H 3C,9G 3C,4H 1C,4G 0 4H 0 0 2C,9H 2H,8G 1C     2C,9H      ##STR308##      0.4 4S,7G,6Y 3C,5G 9C 1C,3H 1C 0 0 1C,5H 0 0 2C,7G 2C,8G 1C,7G 2C,9G      ##STR309##      0.4 2C,6G 1C,3G 1C 1C 0 0 1C,3G 1C,4G 0 0 1C,3H 4H 2C,7G 2C,7G      ##STR310##      0.4 5C,8G,6Y 3C,2H 10C 2C,9H 2C,9G 2G 2C,4G 2C,8H 1C,2G 1C,6G 2C,9H     3C,6G 1C,9G 2C,9H      ##STR311##      0.4 9D,9G,6Y 3C,3H,9G 10C 3C,8G 1C,5G 1C,5G 2C 2C,9H 0 4G 2C,9H     2C,7G,5X 2C,9G 2C,9G      ##STR312##      0.4 3C,7G,6Y 3B 1C,9G 2H 1C,4G 0 3G 1C,3H 0 0 6G 2H,6G 5G 3G        Pre-emergence        Barn-         Morning- Cockle-  Nut- Crab- yard     Wild  kg/ha glory bur Cassia sedge grass grass oats Wheat Corn Soybean     Rice Sorghum      ##STR313##      0.4 9G 9G 9G 10E 9G,5C 9H 9G,2C 9H 9G 9H 10E 9G,1C      ##STR314##      0.4 9G 9G 9G 10E 10E 10H 5C,9H 9H 10H 9H 10E 9H      ##STR315##      2 9G 9G 9G 10E 1C,9G 9H1C,8G 9H 9G 9H 10E 5C,9H    " 0.4 9G 9G 9G 10E     2C,9G 5C,9H 1C,9G 9H 1C,9G 9H 10E 1C,9G      ##STR316##      2 9G 9G 8G 9G 3G 9H 2G 5G 2C,8G 3H 9H 8H    " 0.4 9G 9G 1C,7G 8G 2G 7G     0 0 1C,6G 2H 9H 1C,8H      ##STR317##      0.4 9G 9G 7G 9G 4G 9H 6G 8G 2C,9G 5H 9H 2C,9G      ##STR318##      2 9C 9G 9G 10E 9H 10H 2C,8G 10H 10E 10E 10E 10H    " 0.4 9G 9G 9G 10E     9H 10H 2C,9G 10E 10E 9H 10E 10H      ##STR319##      2 9G 9G 2H 0 0 0 0 0 0 0 3G 2G    " 0.4 5G 4G 0 0 0 0 0 0 0 0 0 0      ##STR320##      2 9G 9G 10E 9G 2C,9G 9H 2C,8H 9G 2C,9G 9H 10E 9H    " 0.4 9G 8G 9G 6G     7G 9H 8G 8G 2C,9G 8H 9H 9G      ##STR321##      2 9G 9G 7G 9G 4G 9H 7G 9G 9G 4H 10E 9H      ##STR322##      2 4G 2G 6G 5G 0 2C,5G 1C 1C 3G 0 8H 2G    " 0.4 9G 8G 5G 0 3G 5G 0 0 3G     0 7G 4G      ##STR323##      0.4 8G 8G 2G 8G 0 1C,9G 1G 1G 1C,5G 1H 8H 2C,8G      ##STR324##      0.4 9G 9G 9G 9G 3C,8G 9H 2C,8G 9H 2C,9G 8H 10E 10H      ##STR325##      0.4 3G 0 0 0 0 0 0 0 0 0 0 1C      ##STR326##      0.4 8G 8G 0 0 1C 2C,8H 2G 2G 1C,3G 0 1C,7G 1C,8G      ##STR327##      1/10 9G 9G 1C,9G 10E 1C,9G 2C,9H 2C,9G 9G 1C,9G 9H 10E 9H      ##STR328##      2 9G 9G 1C,9G 10E 4G 2C,9H 2C,9G 9G 3U,9G 9H 10E 10H    " 0.4 9G -- 8G     9G 0 2C,9H 8G 5G 1C,9G 2C,8H 10E 2C,9H      ##STR329##      2 7G 8G 5H 0 0 2C 0 0 2C 1C,5H 2G 0    " 0.4 5G 5G 0 0 0 0 0 0 0 0 0 0      ##STR330##      0.4 9G 9G 9G 10E 1C 9G 5C 9H 4C 9H 2C 9H 9G 9H 10E 9H      ##STR331##      2 9G 9H 9G 10E 1C 8G 9H 6G 8H 1C 9G 9H 10E 1C 9G    " 0.4 9G 9H 7G 9G     2G 1C 9H 5G 6G 1C 9G 2G 7H 9H 9G      ##STR332##      0.4 9G 9H 9G 10E 2C 9G 3C 9H 2C 9H 1C 9G 9G 8H 10E 3C      ##STR333##      0.4 9G 9H 9G 10E 5C 9G 9H 9H 10E 10E 9H 10E 10E      ##STR334##      0.4 9G 9H 1C 8G 7G 1C 6G 9H -- 1C 8G 1C 9G 1C 4H 9H 4C      ##STR335##      0.4 9G 9H 2C 9G 1C 9G 1C 5G 9H 1C 7G 9G 2U 9G 1C 4H 9H 1C 9G      ##STR336##      0.4 9G 9G 9G 9G 2G 2C,9H 1C,6G 3G 9H 1H,3G 9H 9H      ##STR337##      0.4 9G 8G 9G 5G 1C,5G 2C,9H 5G 0 1C,6G 2C 1C,8H 1C,9G      ##STR338##      0.4 9G 9H 8G 7G 1C 1C,5G 3G 0 1C,6G 3G 1C,6G 1C,8G      ##STR339##      0.4 10E 8G 8G 3G 0 2C,8G 2G 2G 2C,7G 1C,2H 9H 1C,9G      ##STR340##      0.4 10E 9G 5G 4G 0 2C,5G 0 3G 1C,7G 2C 9H 1C,9G      ##STR341##      0.4 9G 9H 8G 4G 3G 1C,9H 1C,7G 1C,8G 1U,9G 1C,1H 9H 9H      ##STR342##      0.4 8G 8H 7G 6G 2G 1C,6G 3G 3G 1C,8G 1H 10E 9H      ##STR343##      0.4 8G 9H 5G 0 0 4G 0 0 1C,3G 2G 9H 1C,9G

Test B

Two plastic bulb pans were filled with fertilized and limed Fallsingtonsilt loam soil. One pan was planted with corn, sorghum, Kentuckybluegrass and several grassy weeds. The other pan was planted withcotton, soybeans, purple nutsedge (Cyperus rotundus), and severalbroadleaf weeds. The following grassy and broadleaf weeds were planted:crabgrass (Digitaria sanguinalis), barnyardgrass (Echinochloacrusgalli), wild oats (Avena fatua), johnsongrass (Sorghum halepense),dallisgrass (Paspalum dilatatum), giant foxtail (Setaria faberii),cheatgrass (Bromus secalinus), mustard (Brassica arvensis), cocklebur(Xanthium pennsylvanicum), pigweed (Amaranthus retroflexus),morningglory (Ipomoea hederacea), cassia (Cassia tora), teaweed (Sidaspinosa), velvetlead (Abutilon theophrasti), and jimsonweed (Daturastramonium). A 12.5 cm diameter plastic pot was also filled withprepared soil and planted with rice and wheat. Another 12.5 cm pot wasplanted with sugarbeets. The above four containers were treatedpreemergence with several test compounds within the scope of theinvention.

Twenty-eight days after treatment, the plants were evaluated andvisually rated for response to the chemical treatments utilizing therating system described previously for Test A. The data are summarizedin Table B. Note that certain compounds are useful as preemergencetreatments for weed control in crops such as soybeans and wheat.

      PRE-EMERGENCE ON FALLSINGTON SILT LOAM        Rate Crab- Barnyard-  Wild Johnson-  Giant       kg/ha grass grass     Sorghum Oats grass Dallisgrass foxtail Ky. bluegrass Cheatgrass Sugarbeet     s Corn Mustard      ##STR344##      0.007 0 5G 6G,3H 2G 4G 5G 3G 5G 7G 4G 5G,3H 7G    " 0.03 0 6G,3C 9G,5H     3G 6G,5H 5G 4G,2C 8G,4C 8G,8C 7G,4C 7G,7H 7G,3C    " 0.06 4G 8G,5H 10E     3G 7G,5H 6G 8G,7C 8G,8C 8G,9C 8G,8C 8G,8H 7G,5C      ##STR345##      0.06 0 0 0 0 0 0 0 4G 5G 7G,5C 0 6G    " 0.25 4G 4G 4G 0 3G 5G 3G 8G     8G,5H 7G,8C 0 7G      ##STR346##      0.06 5G 5G 4G 0 5G 8G 6G 8G,5C 10E -- 5G 8G    " 0.25 9G,8C 7G,5C 8G,3H     0 7G 9G,8C 8G,5H 10C 10E -- 7G,5H 10C      ##STR347##      0.03 0 4G 7G,5H 0 7G 5G 5G 6G,3C 3C 3G 0 6G    " 0.125 6G,2C 8G,5C     9G,9C 4G 8G,4C 7G 8G 8G,7C 9G,9C 7G,6C 0 8G,3C      ##STR348##      0.03 0 0 6G,3H 0 5G,5H 3G 3G 7G,3C 8G,8C 5G,3C 5G,3H 7G    " 0.125     9G,8C 9G,8C 10C 6G,4C 8G,5H 8G,5H 9G,9C 7G,5C 10E 7G,7C 8G,5H 8G,5C      ##STR349##      0.03 5G 8G,5C 10C 6G,5C 8G,3C 8G,4C 7G,3C 7G,7C 10E 7G,7C 7G,3H 8G,3C      " 0.125 7G,2C 9G,9C 10C 7G,6C 9G,9C 9G,9C 10C 8G,9C 10E 7G,7C 10C 9G,5C      ##STR350##      0.06 0 0 9 0 0 0 0 0 0 0 0 5G    " 0.25 0 3G 3G 0 0 4G 5G 5G 4G 3G,4C 0     6G      ##STR351##      0.03 0 0 0 0 0 0 5G 5G 4G 0 0 6G    " 0.125 0 3G 4G,2H 2G 3G 3G 8G 7G     8G,3C 2G 0 7G      ##STR352##      0.06 0 4G 6G,3H 0 0 3G -- 5G 6G 5G 0 6G    " 0.25 0 4G,3C 10C 3G 4G,3H     -- 9G 6G,3H 7G,4C 7G,3C 6G,5H 7G      ##STR353##      0.06 0 2G 0 0 0 -- 3G 4G 7G 4G 0 6G    " 0.25 3G 7G,3H 6G,3H 6G 5G,3H     6G 10E 6G,3C 8G,8C 6G,3H 6G,3H 6G        Rate     Morning-   Velvet- Jimson-     kg/ha Cocklebur Pigweed     Nutsedge Cotton glory Cassia Teaweed leaf weed Soybean Rice Wheat      ##STR354##      0.007 3G 3G 6G 3G 0 0 0 0 0 3G 7G,7C 3G    " 0.03 7G 10E 8G 5G,3H 7G     8G,8C 10C 4G 3G 0 10E 5G     " 0.06 7G 10E 9G 6G,3H 8G 8G,8C 10C 6G,2C     3G 6G,5H 10E 6G,3C      ##STR355##      0.06 0 0 0 0 0 0 0 0 0 2G 3G 0    " 0.25 3G 3G 0 0 5G 0 0 0 0 7G,5H     6G,3H 3G      ##STR356##      0.06 0 -- 8G 4G 0 6G 10C 2G 0 6G,3H 7G,5C 5G    " 0.25 7G -- 10E 7G 6G     7G 10C 5G,3H 5G 7G,5H 10E 7G,4C      ##STR357##      0.03 0 -- 5G 0 0 0 3G 0 0 0 6G,6C 2G    " 0.125 0 -- 9G 7G 4G 6G,4C     5G,5C 0 4G 2H 10C 5G      ##STR358##      0.03 7G,5H -- 7G 5G 0 6G 5G 0 4G 0 6G,3H 3G    " 0.125 8G,8H -- 9G 6G     7G 7G,3C 5G 7G,8C 5G 3G 10E 4G      ##STR359##      0.03 7G,5H -- 10E 6G 3G 6G 5G 0 3G 0 10E 7G,5C    " 0.125 8G,8H -- 10E     8G 8G 7G,3C 7G 6G,5C 7G,5C 3G 10E 8G,7C      ##STR360##      0.06 0 -- 0 0 0 0 -- 3G 0 0 0 0    " 0.25 -- -- 5G 0 0 0 4G 3G,3H 0 2G     0 0      ##STR361##      0.03 6G -- 4G 0 0 0 0 0 0 0 0 0    " 0.125 7G,3H -- 3G 0 0 4G 5G 0 0 0     2G 0      ##STR362##      0.06 -- -- 5G 0 0 4G 0 0 0 0 5G 4G    " 0.25 5G -- 5G 6G,3H 6G 6G 0 0 0     0 7G,5C 4G      ##STR363##      0.06 4G -- 0 3G 3G 2G 0 0 0 0 3G 2G    " 0.25 5G,3H -- 6G 6G,3H 7G 5G 0     3G 0 2H 6G 3G

Test C

Twenty-five cm diameter plastic pots filled with Fallsington silt loamwere planted to soybeans, cotton, alfalfa, corn, rice, wheat, sorghum,velvetleaf (Abutilon theophrasti), sesbania (Sesbania exaltata), Cassia(Cassia tora), morningglory (Ipomoea hederacea), jimsonweed (Daturastramonium), cocklebur (Xanthium pennsylvanicum), crabgrass (Digitariaspp.), nutsedge (Cyperus rotundus), barnyardgrass (Echinochloacrusgalli), giant foxtail (Setaria faberii) and wild oats (Avena fatua).Approximately 21/2 weeks after planting, the young plants and the soilaround them were sprayed overall with the test chemicals dissolved in anon-phytotoxic solvent. Fourteen days after treatment, all species werecompared to untreated controls and visually rated for response totreatment. The rating system was as described previously for Test A. Thedata are presented in Table B. It is evident that the test compoundspossess high postemergence activity.

                                      TABLE C                                     __________________________________________________________________________    OVER-THE-TOP-SOIL/FOLIAGE TREATMENT                                                    ##STR364##                                                                                           ##STR365##                                            Rate kg/ha                                                                    0.03     0.06     0.25      0.007     0.03                            __________________________________________________________________________    Soybeans                                                                              10G,9C   10G,9C   10G,9C    10G,5C    10G,7C                          Velvetleaf                                                                            5G       10G,7C   10C       7G,3C     10G,7C                          Sesbania                                                                              10G,7C   10G,9C   10C       --        2C,3G                           Cassia  8G       7G       10G,4C    5G,2C     7G,3C                           Cotton  10G,6C   10C      10G,9C    7G,1C     8G,2C                           Morningglory                                                                          10G,6C   10C      10G,8C    9G,1C     9G,3C                           Alfalfa 10G,6C   10G,6C   10C       --        7C                              Jimsonweed                                                                            8G       9G,2C    10G,7C    0         0                               Cocklebur                                                                             0        7G,3H    10G,9C    1G        6G,2C                           Corn    9G,3U    10G,6U   10G,9C    7G,5H     7G,3C                           Crabgrass                                                                             0        4G       9G        1G        2G                              Rice    10G,4C   10G,6C   10G,6C    8G,1C     8G,3C                           Nutsedge                                                                              7G       10G,2C   10G,8C    5G        8G                              Barnyardgrass                                                                         10G,5C   10G,6C   10G,9C    7G,1C     8G,3C                           Wheat   10G,2C   10G,3C   10G,3C    2G        4G,2C                           Giant Foxtail                                                                         10G,2C   10G,3C   10G,6C    3G        5G                              Wild Oats                                                                             10G,2C   10G,2C   10G,4C    0         1G                              Sorghum 10G,3C   10G,5C   10C       3G        3G                              __________________________________________________________________________

Test D

Purple nutsedge (Cyperus rotundus) tubers were planted about 2 cm deepin Fallsington silt loam soil contained in 10 cm diameter plastic pots.Five tubers were planted in each pot. Compounds of this invention weredissolved in an non-phytotoxic diluent and sprayed at 560 l/ha in fourmethods of application: soil surface, tuber/soil, soil incorporated, andpostemergence. The soil surface spray consisted of spraying the comoundon the surface of the firmed covering soil. The tuber/soil sprayconsisted of spraying the compound on exposed tubers and subtending soilbefore adding the untreated covering soil. Soil incorporated treatmentconsisted in mixing the compound with the covering soil before using itto cover the tubers. The postemergence treatment was sprayed on nutsedgefoliage and the surrounding soil surface when nutsedge had emerged andgrown to a height of about 12 cm. Pots receiving the postemergencetreatments were placed directly in the greenhouse. Pots receiving theother treatments were misted with about 0.3 cm water before beingtransferred to the greenhouse. Response ratings assessed after fourweeks are recorded in Table D based on the same rating system asdescribed in Test A. The data indicate that the compounds tested arehighly active for the control of nutsedge.

                  TABLE D                                                         ______________________________________                                         RESPONSE OF NUTSEDGE                                                         ______________________________________                                         ##STR366##                                                                          RESPONSE RATING AFTER 4 WEEKS                                                   Pre-emerg. Tuber    Soil                                             Rate kg/ha                                                                             Surface    Spray    Incorp.                                                                             Post-emerg.                                ______________________________________                                        0.125    7G         7G       7G    2G                                         0.50     9G         9G       9G    2G                                         ______________________________________                                         ##STR367##                                                                          RESPONSE RATING AFTER 4 WEEKS                                                   Pre-emerg. Tuber    Soil                                             Rate kg/ha                                                                             Surface    Spray    Incorp.                                                                             Post-emerg.                                ______________________________________                                        0.03      8G        8E,9G    6E,9G 3C,5G                                      0.125    10E        10E      10E   2C,6G                                      ______________________________________                                    

What is claimed is:
 1. A compound selected from ##STR368## R₂ is H, CH₃,OCH₃, F, Cl, Br, NO₂, CF₃, COR₅, S(O)_(m) R₁₀, SO₂ NR₁₀ R₁₁, SO₂ OCH₂CF₃, SO₂ OCH₂ CCl₃ or SO₂ N(OCH₃)CH₃ ;R₃ is H, F, Cl, Br, alkyl C₁ -C₄or CH₃ O; R₄ is H, Cl, Br, F, alkyl C₁ -C₄, alkoxy C₁ -C₄, NO₂, CO₂ R₆or R₁₃ --S--; R₅ is alkoxy C₁ -C₆ ; alkenyloxy C₃ -C₆ ; haloalkoxy C₂-C₆ substituted with 1 to 3 halogens selected from Cl, F and Br;cycloalkoxy C₅ -C₆ ; O--CH₂ CH₂ O)_(n) R₇ ; OCH₂ CH₂ CH₂ OR₇ ; NR₈ R₉ ;N(OCH₃)CH₃ or C₁ -C₄ alkylthio; R₆ is alkyl C₁ -C₆ ; R₇ is alkyl C₁ -C₂; R₈ and R₉ are independently H or alkyl C₁ -C₄ or R₈ and R₉ may betaken together to be (CH₂)₄, (CH₂)₅ or O(CH₂ CH₂ --)₂ ; and R₈ can alsobe ##STR369## R₁₀ and R₁₁ are independently C₁ -C₆ alkyl or C₃ -C₄alkenyl or R₁₀ and R₁₁ can be taken together to be (CH₂)₄, (CH₂)₅ orO(CH₂ CH₂)₂ ; R₁₂ is C₁ -C₁₂ alkyl; CH₂ CH₂ OCH₃ ; CH₂ CH₂ OCH₂ CH₃ ;CH₂ CH₂ CH₂ OCH₃ ; ##STR370## R₁₃ is C₁ -C₃ alkyl; R₁₄ is H, F, Cl, Br,NO₂, CN, CF₃, C₁ -C₃ alkyl, OCH₃ or CH₃ S; R₁₅ is H, F, Cl, Br, CH₃ orOCH₃ ; X is H, CH₃, CH₃ O, Cl or OCH₂ CH₃ ; Y is CH₂ or O; A is CO₂ H,CO₂ B, CONH₂, phenyl, CN, C₂ -C₄ alkenyl, C₂ -C₄ alkynyl, phenylsubstituted with one or two methyl groups or with one or two chlorines;B is C₁ -C₄ alkyl; m is 0, 1 or 2; n is 1 or 2 Z is 0 or 1; W is oxygenor sulfur; provided that (i) when R₁ is ##STR371## then R₂ is NO₂, COR₅,SO₂ NR₁₀ R₁₁, SO₂ N(CH₃)(OCH₃) or SO₂ R₁₀ ; R₄ is other than H; and X isCH₃ or OCH₃ ; (ii) when W is sulfur; when Y is oxygen and theiragriculturally suitable salts.
 2. A compound of claim 1 wherein W isoxygen.
 3. A compound of claim 2 wherein R is ##STR372##
 4. A compoundof claim 3 wherein R₁ is ##STR373##
 5. A compound of claim 4 wherein Xis H, CH₃ or OCH₃.
 6. A compound of claim 5 wherein R₂ is NO₂, COR₅, SO₂NR₁₀ R₁₁ or SO₂ N(OCH₃)(CH₃) and where R₁₀ and R₁₁ are independently CH₃or CH₃ CH₂.
 7. A compound of claim 6 wherein R₃ is H.
 8. A compound ofclaim 7 wherein R₅ is C₁ -C₃ alkoxy or allyloxy.
 9. The compound ofclaim 1 which isN-[(6,7-dihydro-4-methyl-5H-cyclopentapyrimidin-2-yl)aminocarbonyl]-2-nitrobenzenesulfonamide.10. The compound of claim 1 which is2-[[(6,7-dihydro-4-methyl-5H-cyclopentapyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzoicacid, methyl ester.
 11. The compound of claim 1 which isN-[(6,7-dihydro-4-methoxy-5H-cyclopentapyrimidin-2-yl)aminocarbonyl]-2-nitrobenzenesulfonamide.12. The compound of claim 1 which is2-chloro-N-[(5,6-dihydro-4-methylfuro[2,3-d]-pyrimidin-2-yl)aminocarbonyl]benzenesulfonamide.13. The compound of claim 1 which isN-[(5,6-dihydro-4-methylfuro[2,3-d]pyrimidin-2-yl)-aminocarbonyl]-2-nitrobenzenesulfonamide.14. The compound of claim 1 which is2-{[(5,6-dihydro-4-methylfuro[2,3-d]pyrimidin-2-yl)-aminocarbonyl]aminosulfonyl}benzoicacid, methyl ester.
 15. The compound of claim 1 which isN'-[(5,6-dihydro-4-methylfuro[2,3-d]pyrimidin-2-yl)aminocarbonyl]-N,N-dimethyl-1,2-benzenedisulfonamide.16. The compound of claim 1 which is2-{[(6,7-dihydro-4-methyl-5H-cyclopentapyrimidin-2-yl)aminocarbonyl]aminosulfonyl}benzoicacid, ethyl ester.
 17. The compound of claim 1 which is2-{[(5,6-dihydro-4-methylfuro[2,3-d]pyrimidin-2-yl)aminocarbonyl]aminosulfonyl}benzoicacid, ethyl ester.
 18. The compound of claim 1 which is2-{[(5,6-Dihydro-4-methoxyfuro[2,3-d]pyrimidin-2-yl)-aminocarbonyl]aminosulfonyl}benzoicacid, methyl ester.
 19. The compound of claim 1 which is2-[[(5,6-Dihydro-4-methoxyfuro[2,3-d]pyrimidin-2-yl)-aminocarbonyl]aminosulfonyl]benzenecarbothioicacid, methyl ester.
 20. The compound of claim 1 which is1-[2-[[(5,6-Dihydro-4-methoxyfuro[2,3-d]pyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzoyl]pyrrolidine.21. The compound of claim 1 which is2-[[(5,6-Dihydro-4-methylfuro[2,3-d]pyrimidin-2-yl)-aminocarbonyl]aminosulfonyl]-N,N-dimethylbenzamide.22. The compound of claim 1 which is2-{[(4-Chloro-5,6-dihydrofuro[2,3-d]pyrimidin-2-yl)-aminocarbonyl]aminosulfonyl}benzoicacid, methyl ester.
 23. The compound of claim 1 which is2-{[(6,7-Dihydro-4-methyl-5H-pyrano[2,3-d]pyrimidin-2-yl)aminocarbonyl]aminosulfonyl}benzoicacid, methyl ester.
 24. The compound of claim 1 which is2-{[(6,7-Dihydro-4-methoxy-5H-pyrano[2,3-d]pyrimidin-2-yl)aminocarbonyl]aminosulfonyl}benzoicacid, methyl ester.
 25. A composition for the control of undesirablevegetation consisting essentially of an herbicidally effective amount ofa compound of any of claims 1-24 and at least one of (a) a surfaceactive agent, and (b) a solid or liquid diluent.
 26. A method for thecontrol of undesirable vegetation comprising applying to the locus ofsuch undesirable vegetation an herbicidally effective amount of acompound of any of claims 1-24.
 27. A method for the control of nutsedgecomprising applying to the locus of such nutsedge an herbicidallyeffective amount of a compound of any of claims 1-24.
 28. A compoundselected from: ##STR374## R₂ is H, CH₃, OCH₃, F, Cl, Br, NO₂, CF₃, COR₅,S(O)_(m) R₁₀, SO₂ NR₁₀ R₁₁, SO₂ OCH₂ CF₃, SO₂ OCH₂ CCl₃ or SO₂N(OCH₃)CH₃ ;R₃ is H, F, Cl, Br, alkyl C₁ -C₄ or CH₃ O; R₄ is H, Cl, Br,F, alkyl C₁ -C₄, alkoxy C₁ -C₄, NO₂, CO₂ R₆ or R₁₃ --S--; R₅ is alkoxyC₁ -C₆ ; alkenyloxy C₃ -C₆ ; haloalkoxy C₂ -C₆ substituted with 1 to 3halogens selected from Cl, F and Br; cycloalkoxy C₅ -C₆ ; O--CH₂ CH₂O)_(n) R₇ ; OCH₂ CH₂ CH₂ OR₇ ; NR₈ R₉ ; N(OCH₃)CH₃ or C₁ -C₄ alkylthio;R₆ is alkyl C₁ -C₆ ; R₇ is alkyl C₁ -C₂ ; R₈ and R₉ are independently Hor alkyl C₁ -C₄ or R₈ and R₉ may be taken together to be (CH₂)₄, (CH₂)₅or O(CH₂ CH₂ --)₂ ; and R₈ can also be ##STR375## R₁₀ and R₁₁ areindependently C₁ -C₆ alkyl or C₃ -C₄ alkenyl or R₁₀ and R₁₁ can be takentogether to be (CH₂)₄, (CH₂)₅ or O(CH₂ CH₂)₂ ; R₁₂ is C₁ -C₁₂ alkyl; CH₂CH₂ OCH₃ ; CH₂ CH₂ OCH₂ CH₃ ; CH₂ CH₂ CH₂ OCH₃ ; ##STR376## R₁₃ is C₁-C₃ alkyl; R₁₄ is H, F, Cl, Br, NO₂, CN, CF₃, C₁ -C₃ alkyl, OCH₃ or CH₃S; R₁₅ is H, F, Cl, Br, CH₃ or OCH₃ ; X is H, CH₃, CH₃ O, Cl or OCH₂ CH₃; A is CO₂ H, CO₂ B, CONH₂, phenyl, CN, C₂ -C₄ alkenyl, C₂ -C₄ alkynyl,phenyl substituted with one or two methyl grohups or with one or twochlorines; B is C₁ -C₄ alkyl; m is 0, 1 or 2; n is 1 or 2; and Z is 0 or1; provided that (i) when R₁ " is ##STR377## then R₂ is NO₂, COR₅, SO₂NR₁₀ R₁₁, SO₂ N(CH₃)(OCH₃) or SO₂ R₁₀ ; R₄ is other than H; and X is CH₃or OCH₃.